Reversal of Diastereoselection in the Conjugate Addition of Cuprates to Unsaturated Lactams

被引：18

作者：

Wright, Stephen W. ^{[1
]}

Choi, Chulho ^{[1
]}

Chung, Seungwon ^{[1
]}

Boscoe, Brian P. ^{[1
]}

Drozda, Susan E. ^{[1
]}

Mousseau, James J. ^{[1
]}

Trzupele, John D. ^{[2
]}

机构：

[1] Pfizer Global Res & Dev, Worldwide Med Chem, Groton, CT 06340 USA

[2] Pfizer Global Res & Dev, Inflammat & Immunol Res, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 21期

关键词：

STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; PYROGLUTAMIC ACID; REAGENTS;

D O I：

10.1021/acs.orglett.5b02533

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report that the stereochemical outcome of the conjugate addition of organocopper reagents to bicyclic alpha,beta-unsaturated lactams derived from pyroglutaminol is determined by the nature of the aminal group. Bicyclic alpha,beta-unsaturated lactams in which the aminal is derived from a ketone have been found to afford products of syn conjugate addition. By contrast, bicyclic alpha,beta-unsaturated lactams in which the aminal is derived from an aldehyde afford products of anti conjugate addition. These remarkably different results obtained from very similar starting materials are unexpected.

引用

页码：5204 / 5207

页数：4

共 50 条

[21] Diastereoselective Synthesis of γ-Lactams and δ-Lactams via a Conjugate Addition-Initiated Tandem Reaction
Gan, Miaomiao
Jiang, Lan
Li, Zhengning
SYNLETT, 2019, 30 (12) : 1447 - 1451
[22] Conjugate Addition of 2-Acetylindole Enolates to Unsaturated Oxazolopiperidone Lactams: Enantioselective Access to the Tetracyclic Ring System of Ervitsine
Amat, Mercedes
Checa, Begona
Llor, Nuria
Perez, Maria
Bosch, Joan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 898 - 907
[23] CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO UNSATURATED ESTERS
SAKATA, H
KUWAJIMA, I
TETRAHEDRON LETTERS, 1987, 28 (46) : 5719 - 5722
[24] Catalytic nucleophilic addition of terminal alkynes to α,β-unsaturated-γ-lactams
Wang, Maorong
Gao, Bao
Huang, Hanmin
CHINESE JOURNAL OF CATALYSIS, 2016, 37 (04) : 476 - 483
[25] Michael addition of nitroalkanes to nonactivated α,β-unsaturated δ-thiolactams: reactivity, diastereoselectivity, and comparison to α,β-unsaturated δ-lactams
Sosnicki, Jacek G.
TETRAHEDRON, 2009, 65 (07) : 1336 - 1348
[26] Conjugate addition of mixed diorganozinc compounds and functionalized organozinc cuprates to nitroolefins
Rimkus, A
Sewald, N
ORGANIC LETTERS, 2002, 4 (19) : 3289 - 3291
[27] ENANTIOSELECTIVE CONJUGATE ADDITION TO CYCLIC ENONES WITH (S)-MAPP-CUPRATES
ROSSITER, BE
EGUCHI, M
HERNANDEZ, AE
VICKERS, D
MEDICH, J
MARR, J
HEINIS, D
TETRAHEDRON LETTERS, 1991, 32 (32) : 3973 - 3976
[28] THE INFLUENCE OF THE AROMATIC SUBSTITUENT ON THE REACTIVITY OF MAPP CUPRATES IN ENANTIOSELECTIVE CONJUGATE ADDITION
ROSSITER, BE
MIAO, G
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 189 - ORGN
[29] Conjugate addition of organocopper reagents in dichloromethane to α,β-unsaturated esters
Yang, Jingyue
Dudley, Gregory B.
TETRAHEDRON LETTERS, 2007, 48 (44) : 7887 - 7889
[30] Conjugate addition of nitrogen nucleophiles to an unsaturated pyrrolidinone.
Chan, PWH
Cottrell, IF
Moloney, MG
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 215 : U18 - U18

← 1 2 3 4 5 →