Catalytic Enantioselective C-C Bond-Forming Reactions of Deconjugated Butyrolactams: Michael Addition to α,β-Unsaturated Aldehydes and Ketones

被引：15

作者：

Roy, Soumya Jyoti Singha ^{[1
]}

Mukherjee, Santanu ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

关键词：

GAMMA-BUTYROLACTAM; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; BUTENOLIDES; LACTAMS; HYDROGENATION; DIVERSITY;

D O I：

10.1021/acs.joc.8b02051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic reactivity of deconjugated butyrolactams has been demonstrated for enantioselective Michael additions to alpha,beta-unsaturated aldehydes and ketones. These reactions are catalyzed by diphenylprolinol silyl ether and trans-1,2-diaminocyclohexane-derived bifunctional primary aminothiourea, respectively, producing the Michael adducts with moderate diastereoselectivities and good to excellent enantioselectivities (up to 99:1 er). Unlike in the case of structurally related deconjugated butenolides where vinylogous addition is prevalent, an exclusive alpha-addition is observed for deconjugated butyrolactams.

引用

页码：12071 / 12085

页数：15

共 50 条

[1] Catalytic enantioselective Michael addition of deconjugated butyrolactams to maleimides
Ray, Bidisha
Mukherjee, Santanu
TETRAHEDRON, 2019, 75 (24) : 3292 - 3298
[2] Highly efficient C-C bond-forming reactions of an α-cyanoketene dithioacetal with aldehydes and ketones
Zhang, Qian
Liu, Yu
Wang, Mang
Liu, Qun
Hu, Jianglei
Yin, Yanbing
SYNTHESIS-STUTTGART, 2006, (18): : 3009 - 3014
[3] Synthesis and stereoselective C-C bond-forming reactions of peptide aldehydes
Reetz, MT
Griebenow, N
LIEBIGS ANNALEN, 1996, (03): : 335 - 348
[4] Catalytic addition of metallo-aldehyde enolates to ketones: A new C-C bond-forming hydrogenation
Koech, PK
Krische, MJ
ORGANIC LETTERS, 2004, 6 (05) : 691 - 694
[5] ASYMMETRIC C-C BOND-FORMING REACTIONS
MEYERS, AI
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 161 - ORGN
[6] Enantioselective C-C bond-forming reactions using vanadium(V) complexes
Takizawa, Shinobu
Kodera, Junpei
Rajesh, Doss
Katayama, Tomomi
Sasai, Hiroaki
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
[7] New catalytic C-C bond-forming reactions with carbon dioxide.
Sadighi, JP
Sirokman, G
Smythe, NA
Laitar, DS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U971 - U971
[8] Recent advances in asymmetric catalytic C-C bond-forming reactions.
Zhang, XM
Cao, P
Wang, B
Hu, XQ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U150 - U150
[9] Exploiting β-Amino Acid Enolates in Direct Catalytic Diastereo- and Enantioselective C-C Bond-Forming Reactions
Yu, Jin-Sheng
Noda, Hidetoshi
Shibasaki, Masakatsu
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (59) : 15796 - 15800
[10] Hydrogen-bond-promoted C-C bond-forming reaction: Catalyst-free Michael addition reactions in ethanol
Shirakawa, Seiji
Shimizu, Shoichi
SYNLETT, 2007, (20) : 3160 - 3164

← 1 2 3 4 5 →