N ‐Heterocyclic Carbene‐Catalyzed Kinetic Resolution of 3‐Nitro‐1,2‐Dihydroquinolines: Asymmetric Synthesis of All C 2 ‐, C 3 ‐ and C 4 ‐Functionalized Tetrahydroquinolines
An efficient N ‐heterocyclic carbene (NHC)‐catalyzed kinetic resolution of 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (DHQs) allowing the synthesis of densely functionalized enantioenriched tetrahydroquinolines through the resolution at remote stereocenter is described. The Re ‐face addition of α ,...
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| Veröffentlicht in: | European journal of organic chemistry 2024-05, Vol.27 (17) |
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| container_title | European journal of organic chemistry |
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| creator | Shukla, Pushpendra Mani Pratap, Aniruddh Maji, Biswajit |
| description | An efficient
N
‐heterocyclic carbene (NHC)‐catalyzed kinetic resolution of 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (DHQs) allowing the synthesis of densely functionalized enantioenriched tetrahydroquinolines through the resolution at remote stereocenter is described. The
Re
‐face addition of
α
,
β
‐unsaturated azolium homoenolate intermediate generated in situ from enal with the more kinetically favored (S)‐enantiomer of the racemic 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (
rac
‐
1
), affording the enantiopure tetrahydroquinolines (up to >99 : 1
dr
, >99 : 1
er
) and the opposite (
R
)‐enantiomer of DHQ (
ent
‐
1
) was recovered (up to >99 : 1
er
). |
| doi_str_mv | 10.1002/ejoc.202301272 |
| format | Article |
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N
‐heterocyclic carbene (NHC)‐catalyzed kinetic resolution of 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (DHQs) allowing the synthesis of densely functionalized enantioenriched tetrahydroquinolines through the resolution at remote stereocenter is described. The
Re
‐face addition of
α
,
β
‐unsaturated azolium homoenolate intermediate generated in situ from enal with the more kinetically favored (S)‐enantiomer of the racemic 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (
rac
‐
1
), affording the enantiopure tetrahydroquinolines (up to >99 : 1
dr
, >99 : 1
er
) and the opposite (
R
)‐enantiomer of DHQ (
ent
‐
1
) was recovered (up to >99 : 1
er
).</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202301272</identifier><language>eng</language><ispartof>European journal of organic chemistry, 2024-05, Vol.27 (17)</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-crossref_primary_10_1002_ejoc_2023012723</cites><orcidid>0000-0002-2855-2371</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Shukla, Pushpendra Mani</creatorcontrib><creatorcontrib>Pratap, Aniruddh</creatorcontrib><creatorcontrib>Maji, Biswajit</creatorcontrib><title>N ‐Heterocyclic Carbene‐Catalyzed Kinetic Resolution of 3‐Nitro‐1,2‐Dihydroquinolines: Asymmetric Synthesis of All C 2 ‐, C 3 ‐ and C 4 ‐Functionalized Tetrahydroquinolines</title><title>European journal of organic chemistry</title><description>An efficient
N
‐heterocyclic carbene (NHC)‐catalyzed kinetic resolution of 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (DHQs) allowing the synthesis of densely functionalized enantioenriched tetrahydroquinolines through the resolution at remote stereocenter is described. The
Re
‐face addition of
α
,
β
‐unsaturated azolium homoenolate intermediate generated in situ from enal with the more kinetically favored (S)‐enantiomer of the racemic 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (
rac
‐
1
), affording the enantiopure tetrahydroquinolines (up to >99 : 1
dr
, >99 : 1
er
) and the opposite (
R
)‐enantiomer of DHQ (
ent
‐
1
) was recovered (up to >99 : 1
er
).</description><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqVkL9OwzAQxi0EEuXPyuwHaMLZjoLCVgWqSpU6QAe2yCQX1ZVrg-0MZuIReCCehifBlhADG8vdT3f33Z0-Qq4YlAyAX-Pe9iUHLoDxG35EZgyapoC6gePElagK1oinU3Lm_R4AmrpmM_K5oV_vHysM6Gwfe6162kr3jAZTuZVB6viGA10rgyH1HtBbPQVlDbUjFWlmo4KzKbM5T_FO7eLg7OukjNVJ42_pwsfDAYNL6sdowg698lm80Jq2lOfz8wQiA5VmSFxlXk6mz4ekVvmDbVoh_yy_ICej1B4vf_I5KZf323ZV9M5673DsXpw6SBc7Bl32qMsedb8eiX8LvgHzmnjJ</recordid><startdate>20240503</startdate><enddate>20240503</enddate><creator>Shukla, Pushpendra Mani</creator><creator>Pratap, Aniruddh</creator><creator>Maji, Biswajit</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2855-2371</orcidid></search><sort><creationdate>20240503</creationdate><title>N ‐Heterocyclic Carbene‐Catalyzed Kinetic Resolution of 3‐Nitro‐1,2‐Dihydroquinolines: Asymmetric Synthesis of All C 2 ‐, C 3 ‐ and C 4 ‐Functionalized Tetrahydroquinolines</title><author>Shukla, Pushpendra Mani ; Pratap, Aniruddh ; Maji, Biswajit</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-crossref_primary_10_1002_ejoc_2023012723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shukla, Pushpendra Mani</creatorcontrib><creatorcontrib>Pratap, Aniruddh</creatorcontrib><creatorcontrib>Maji, Biswajit</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shukla, Pushpendra Mani</au><au>Pratap, Aniruddh</au><au>Maji, Biswajit</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N ‐Heterocyclic Carbene‐Catalyzed Kinetic Resolution of 3‐Nitro‐1,2‐Dihydroquinolines: Asymmetric Synthesis of All C 2 ‐, C 3 ‐ and C 4 ‐Functionalized Tetrahydroquinolines</atitle><jtitle>European journal of organic chemistry</jtitle><date>2024-05-03</date><risdate>2024</risdate><volume>27</volume><issue>17</issue><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient
N
‐heterocyclic carbene (NHC)‐catalyzed kinetic resolution of 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (DHQs) allowing the synthesis of densely functionalized enantioenriched tetrahydroquinolines through the resolution at remote stereocenter is described. The
Re
‐face addition of
α
,
β
‐unsaturated azolium homoenolate intermediate generated in situ from enal with the more kinetically favored (S)‐enantiomer of the racemic 2‐substituted 3‐nitro‐1,2‐dihydroquinolines (
rac
‐
1
), affording the enantiopure tetrahydroquinolines (up to >99 : 1
dr
, >99 : 1
er
) and the opposite (
R
)‐enantiomer of DHQ (
ent
‐
1
) was recovered (up to >99 : 1
er
).</abstract><doi>10.1002/ejoc.202301272</doi><orcidid>https://orcid.org/0000-0002-2855-2371</orcidid></addata></record> |
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| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_202301272 |
| source | Wiley Online Library Journals Frontfile Complete |
| title | N ‐Heterocyclic Carbene‐Catalyzed Kinetic Resolution of 3‐Nitro‐1,2‐Dihydroquinolines: Asymmetric Synthesis of All C 2 ‐, C 3 ‐ and C 4 ‐Functionalized Tetrahydroquinolines |
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