Features of the Baeyer—Villiger reaction in the case of a complex variously functionalized substrate
The reactions of (3 S ,4 RS )-1,3-dideoxy-3-[(2 Z )-4-methoxy-3-methyl-4-oxobut-2-en1-yl]-4- C -methyl-4,5- O -(1-methylethylidene)pent-2-ulose with MCPBA and trifluoroperacetic acid were studied. It was shown that 60% MCPBA in CH 2 Cl 2 at room temperature caused isomerization in the acetonide frag...
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| Veröffentlicht in: | Russian chemical bulletin 2023-10, Vol.72 (10), p.2392-2398 |
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| creator | Sunagatullina, G. R. Khursan, S. L. Lobov, A. N. Selezneva, N. K. Miftakhov, M. S. |
| description | The reactions of (3
S
,4
RS
)-1,3-dideoxy-3-[(2
Z
)-4-methoxy-3-methyl-4-oxobut-2-en1-yl]-4-
C
-methyl-4,5-
O
-(1-methylethylidene)pent-2-ulose with MCPBA and trifluoroperacetic acid were studied. It was shown that 60% MCPBA in CH
2
Cl
2
at room temperature caused isomerization in the acetonide fragment of this compound, while no expected Baeyer—Villiger (B—V) reaction was observed at the methyl ketone. In the MCPBA—AcONa system, the epoxidation of the activated double bond followed the conjugate addition—elimination scheme. The oxidation with trifluoroperacetic acid occurred at the methyl ketone moiety with subsequent decomposition of the dioxolane protecting group and intramolecular lactonization. The introduction into the B—V reaction of the corresponding aldehyde-containing partner instead of the methyl ketone-containing ulose led to an abnormal product of furanization with the loss of the chiral center. |
| doi_str_mv | 10.1007/s11172-023-4038-0 |
| format | Article |
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S
,4
RS
)-1,3-dideoxy-3-[(2
Z
)-4-methoxy-3-methyl-4-oxobut-2-en1-yl]-4-
C
-methyl-4,5-
O
-(1-methylethylidene)pent-2-ulose with MCPBA and trifluoroperacetic acid were studied. It was shown that 60% MCPBA in CH
2
Cl
2
at room temperature caused isomerization in the acetonide fragment of this compound, while no expected Baeyer—Villiger (B—V) reaction was observed at the methyl ketone. In the MCPBA—AcONa system, the epoxidation of the activated double bond followed the conjugate addition—elimination scheme. The oxidation with trifluoroperacetic acid occurred at the methyl ketone moiety with subsequent decomposition of the dioxolane protecting group and intramolecular lactonization. The introduction into the B—V reaction of the corresponding aldehyde-containing partner instead of the methyl ketone-containing ulose led to an abnormal product of furanization with the loss of the chiral center.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-023-4038-0</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Aldehydes ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Dichloromethane ; Epoxidation ; Full Articles ; Inorganic Chemistry ; Isomerization ; Ketones ; Organic Chemistry ; Oxidation ; Room temperature ; Substrates</subject><ispartof>Russian chemical bulletin, 2023-10, Vol.72 (10), p.2392-2398</ispartof><rights>Springer Science+Business Media LLC 2023</rights><rights>Springer Science+Business Media LLC 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c268t-196a176569f12a03e49012fa6ea5e5d3e0793c835be0ab92b2cbecf8274d08333</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-023-4038-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-023-4038-0$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,41467,42536,51297</link.rule.ids></links><search><creatorcontrib>Sunagatullina, G. R.</creatorcontrib><creatorcontrib>Khursan, S. L.</creatorcontrib><creatorcontrib>Lobov, A. N.</creatorcontrib><creatorcontrib>Selezneva, N. K.</creatorcontrib><creatorcontrib>Miftakhov, M. S.</creatorcontrib><title>Features of the Baeyer—Villiger reaction in the case of a complex variously functionalized substrate</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><description>The reactions of (3
S
,4
RS
)-1,3-dideoxy-3-[(2
Z
)-4-methoxy-3-methyl-4-oxobut-2-en1-yl]-4-
C
-methyl-4,5-
O
-(1-methylethylidene)pent-2-ulose with MCPBA and trifluoroperacetic acid were studied. It was shown that 60% MCPBA in CH
2
Cl
2
at room temperature caused isomerization in the acetonide fragment of this compound, while no expected Baeyer—Villiger (B—V) reaction was observed at the methyl ketone. In the MCPBA—AcONa system, the epoxidation of the activated double bond followed the conjugate addition—elimination scheme. The oxidation with trifluoroperacetic acid occurred at the methyl ketone moiety with subsequent decomposition of the dioxolane protecting group and intramolecular lactonization. The introduction into the B—V reaction of the corresponding aldehyde-containing partner instead of the methyl ketone-containing ulose led to an abnormal product of furanization with the loss of the chiral center.</description><subject>Aldehydes</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Dichloromethane</subject><subject>Epoxidation</subject><subject>Full Articles</subject><subject>Inorganic Chemistry</subject><subject>Isomerization</subject><subject>Ketones</subject><subject>Organic Chemistry</subject><subject>Oxidation</subject><subject>Room temperature</subject><subject>Substrates</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kLFOwzAQhi0EEqXwAGyWmA1nu4mdESoKSJVYgNVy3DOkSpNiJ4gy8RA8IU-C2yAxMd0N3__r7iPklMM5B1AXkXOuBAMh2QSkZrBHRjxTkhVc8f20Q56zTOjskBzFuAQAobUeET9D2_UBI2097V6QXlncYPj-_Hqq6rp6xkADWtdVbUOrZkc4G3FLW-ra1brGd_pmQ9X2sd5Q3zc71tbVBy5o7MvYBdvhMTnwto548jvH5HF2_TC9ZfP7m7vp5Zw5keuO8SK3XOVZXnguLEicFMCFtznaDLOFRFCFdFpmJYItC1EKV6LzWqjJArSUckzOht51aF97jJ1Ztn1I50ST_i2SKaF0ovhAudDGGNCbdahWNmwMB7PVaQadJuk0W50GUkYMmZjYJnn5a_4_9AMG_HmL</recordid><startdate>20231001</startdate><enddate>20231001</enddate><creator>Sunagatullina, G. R.</creator><creator>Khursan, S. L.</creator><creator>Lobov, A. N.</creator><creator>Selezneva, N. K.</creator><creator>Miftakhov, M. S.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20231001</creationdate><title>Features of the Baeyer—Villiger reaction in the case of a complex variously functionalized substrate</title><author>Sunagatullina, G. R. ; Khursan, S. L. ; Lobov, A. N. ; Selezneva, N. K. ; Miftakhov, M. S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c268t-196a176569f12a03e49012fa6ea5e5d3e0793c835be0ab92b2cbecf8274d08333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aldehydes</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Dichloromethane</topic><topic>Epoxidation</topic><topic>Full Articles</topic><topic>Inorganic Chemistry</topic><topic>Isomerization</topic><topic>Ketones</topic><topic>Organic Chemistry</topic><topic>Oxidation</topic><topic>Room temperature</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sunagatullina, G. R.</creatorcontrib><creatorcontrib>Khursan, S. L.</creatorcontrib><creatorcontrib>Lobov, A. N.</creatorcontrib><creatorcontrib>Selezneva, N. K.</creatorcontrib><creatorcontrib>Miftakhov, M. S.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sunagatullina, G. R.</au><au>Khursan, S. L.</au><au>Lobov, A. N.</au><au>Selezneva, N. K.</au><au>Miftakhov, M. S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Features of the Baeyer—Villiger reaction in the case of a complex variously functionalized substrate</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2023-10-01</date><risdate>2023</risdate><volume>72</volume><issue>10</issue><spage>2392</spage><epage>2398</epage><pages>2392-2398</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>The reactions of (3
S
,4
RS
)-1,3-dideoxy-3-[(2
Z
)-4-methoxy-3-methyl-4-oxobut-2-en1-yl]-4-
C
-methyl-4,5-
O
-(1-methylethylidene)pent-2-ulose with MCPBA and trifluoroperacetic acid were studied. It was shown that 60% MCPBA in CH
2
Cl
2
at room temperature caused isomerization in the acetonide fragment of this compound, while no expected Baeyer—Villiger (B—V) reaction was observed at the methyl ketone. In the MCPBA—AcONa system, the epoxidation of the activated double bond followed the conjugate addition—elimination scheme. The oxidation with trifluoroperacetic acid occurred at the methyl ketone moiety with subsequent decomposition of the dioxolane protecting group and intramolecular lactonization. The introduction into the B—V reaction of the corresponding aldehyde-containing partner instead of the methyl ketone-containing ulose led to an abnormal product of furanization with the loss of the chiral center.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s11172-023-4038-0</doi><tpages>7</tpages></addata></record> |
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| issn | 1066-5285 1573-9171 |
| language | eng |
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| subjects | Aldehydes Chemistry Chemistry and Materials Science Chemistry/Food Science Dichloromethane Epoxidation Full Articles Inorganic Chemistry Isomerization Ketones Organic Chemistry Oxidation Room temperature Substrates |
| title | Features of the Baeyer—Villiger reaction in the case of a complex variously functionalized substrate |
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