O 2 ‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N ‐ tert ‐Butanesulfinyl Imines To Form syn ‐1,3‐Amino Alcohols
An O 2 ‐assisted, four‐component reaction has been developed to synthesize a wide range of syn ‐1,3‐amino alcohols in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide ( component‐I ) with O 2 ( component‐II ) to give a magnesium enolate of acetaldehyde, which undergoes addit...
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| Veröffentlicht in: | Angewandte Chemie 2021-11, Vol.133 (46), p.24849-24854 |
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| container_title | Angewandte Chemie |
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| creator | Wang, Runping Luo, Jingfan Zheng, Chunmei Zhang, Hongyun Gao, Lu Song, Zhenlei |
| description | An O
2
‐assisted, four‐component reaction has been developed to synthesize a wide range of
syn
‐1,3‐amino alcohols in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide (
component‐I
) with O
2
(
component‐II
) to give a magnesium enolate of acetaldehyde, which undergoes addition to a chiral
N
‐
tert
‐butanesulfinyl imine (
component‐III
) followed by a sequential addition with excess vinyl magnesium bromide (
component‐IV
). The approach allows diastereoselective synthesis of
anti
/
syn
‐ and
syn
/
syn
‐3‐amino‐1,5‐diols in good yields with high diastereoselectivity. The method was illustrated in an efficient, four‐step synthesis of piperidine alkaloid (−)‐2′‐
epi
‐ethylnorlobelol. |
| doi_str_mv | 10.1002/ange.202109566 |
| format | Article |
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2
‐assisted, four‐component reaction has been developed to synthesize a wide range of
syn
‐1,3‐amino alcohols in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide (
component‐I
) with O
2
(
component‐II
) to give a magnesium enolate of acetaldehyde, which undergoes addition to a chiral
N
‐
tert
‐butanesulfinyl imine (
component‐III
) followed by a sequential addition with excess vinyl magnesium bromide (
component‐IV
). The approach allows diastereoselective synthesis of
anti
/
syn
‐ and
syn
/
syn
‐3‐amino‐1,5‐diols in good yields with high diastereoselectivity. The method was illustrated in an efficient, four‐step synthesis of piperidine alkaloid (−)‐2′‐
epi
‐ethylnorlobelol.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202109566</identifier><language>eng</language><ispartof>Angewandte Chemie, 2021-11, Vol.133 (46), p.24849-24854</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-crossref_primary_10_1002_ange_2021095663</cites><orcidid>0000-0002-7228-1572</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Wang, Runping</creatorcontrib><creatorcontrib>Luo, Jingfan</creatorcontrib><creatorcontrib>Zheng, Chunmei</creatorcontrib><creatorcontrib>Zhang, Hongyun</creatorcontrib><creatorcontrib>Gao, Lu</creatorcontrib><creatorcontrib>Song, Zhenlei</creatorcontrib><title>O 2 ‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N ‐ tert ‐Butanesulfinyl Imines To Form syn ‐1,3‐Amino Alcohols</title><title>Angewandte Chemie</title><description>An O
2
‐assisted, four‐component reaction has been developed to synthesize a wide range of
syn
‐1,3‐amino alcohols in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide (
component‐I
) with O
2
(
component‐II
) to give a magnesium enolate of acetaldehyde, which undergoes addition to a chiral
N
‐
tert
‐butanesulfinyl imine (
component‐III
) followed by a sequential addition with excess vinyl magnesium bromide (
component‐IV
). The approach allows diastereoselective synthesis of
anti
/
syn
‐ and
syn
/
syn
‐3‐amino‐1,5‐diols in good yields with high diastereoselectivity. The method was illustrated in an efficient, four‐step synthesis of piperidine alkaloid (−)‐2′‐
epi
‐ethylnorlobelol.</description><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqVjz1OxDAQhS0EEuGnpZ4DsMF2_ki5G7FaCkBCK9rIyjobI9uzsh2hdByBkvNxEmKE6Klmnua9mfkIuWI0ZZTyG2H3MuWUM1oXZXlEElZwtsiqojomCaV5vrjleX1Kzrx_pZSWvKoT8vkEHL7eP5beKx_kDtY4ulk3aA5opQ3wLEUXFFrAHl6UnTQ8iL2VXo0GVg6N2kl4U2GAZlBOaHiM6yBIF2KzGoOYzaPuf6L3Rs0KtjjfcQb8ZKOJXWfxhXmGsNQdDqj9BTnphfby8reek3R9t202i86h90727cEpI9zUMtpG_jbyt3_82b8D3yClabI</recordid><startdate>20211108</startdate><enddate>20211108</enddate><creator>Wang, Runping</creator><creator>Luo, Jingfan</creator><creator>Zheng, Chunmei</creator><creator>Zhang, Hongyun</creator><creator>Gao, Lu</creator><creator>Song, Zhenlei</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-7228-1572</orcidid></search><sort><creationdate>20211108</creationdate><title>O 2 ‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N ‐ tert ‐Butanesulfinyl Imines To Form syn ‐1,3‐Amino Alcohols</title><author>Wang, Runping ; Luo, Jingfan ; Zheng, Chunmei ; Zhang, Hongyun ; Gao, Lu ; Song, Zhenlei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-crossref_primary_10_1002_ange_2021095663</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Runping</creatorcontrib><creatorcontrib>Luo, Jingfan</creatorcontrib><creatorcontrib>Zheng, Chunmei</creatorcontrib><creatorcontrib>Zhang, Hongyun</creatorcontrib><creatorcontrib>Gao, Lu</creatorcontrib><creatorcontrib>Song, Zhenlei</creatorcontrib><collection>CrossRef</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Runping</au><au>Luo, Jingfan</au><au>Zheng, Chunmei</au><au>Zhang, Hongyun</au><au>Gao, Lu</au><au>Song, Zhenlei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>O 2 ‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N ‐ tert ‐Butanesulfinyl Imines To Form syn ‐1,3‐Amino Alcohols</atitle><jtitle>Angewandte Chemie</jtitle><date>2021-11-08</date><risdate>2021</risdate><volume>133</volume><issue>46</issue><spage>24849</spage><epage>24854</epage><pages>24849-24854</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>An O
2
‐assisted, four‐component reaction has been developed to synthesize a wide range of
syn
‐1,3‐amino alcohols in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide (
component‐I
) with O
2
(
component‐II
) to give a magnesium enolate of acetaldehyde, which undergoes addition to a chiral
N
‐
tert
‐butanesulfinyl imine (
component‐III
) followed by a sequential addition with excess vinyl magnesium bromide (
component‐IV
). The approach allows diastereoselective synthesis of
anti
/
syn
‐ and
syn
/
syn
‐3‐amino‐1,5‐diols in good yields with high diastereoselectivity. The method was illustrated in an efficient, four‐step synthesis of piperidine alkaloid (−)‐2′‐
epi
‐ethylnorlobelol.</abstract><doi>10.1002/ange.202109566</doi><orcidid>https://orcid.org/0000-0002-7228-1572</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0044-8249 |
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| issn | 0044-8249 1521-3757 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ange_202109566 |
| source | Wiley Online Library All Journals |
| title | O 2 ‐Assisted Four‐Component Reaction of Vinyl Magnesium Bromide with Chiral N ‐ tert ‐Butanesulfinyl Imines To Form syn ‐1,3‐Amino Alcohols |
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