Direct Catalytic Asymmetric Mannich-Type Reaction of Alkylamides

被引：39

作者：

Arteaga, Fernando Arteaga ^{[1
]}

Liu, Zijian ^{[1
]}

Brewitz, Lennart ^{[1
]}

Chen, Jianyang ^{[1
]}

Sun, Bo ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Inst Microbial Chem Bikaken, Shinagawa Ku, 3-14-23 Kamiosaki, Tokyo 1410021, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 10期

关键词：

ALDOL REACTION; 1,4-ADDITION REACTIONS; BETA-PEPTIDES; AMIDES; ALDEHYDES; ALKYLNITRILES; ACETONITRILE; THIOAMIDES; COMPLEXES; IMINES;

D O I：

10.1021/acs.orglett.6b00879

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct enolate formation coupled with subsequent enantioselective C-C bond formation remains a topic of intense interest in asymmetric catalysis. This methodology is achieved even with low acidic amides without an electron-withdrawing group at the alpha-position in the context of a Mannich-type reaction. Acetate-, propionate-, and butyrate-type 7-azaindoline amides served as enolate precursors to afford the desired Mannich adducts with high stereoselectivity, and ligand-enabled diastereo-divergency provided access to both anti/syn diastereomers. The facile transformation of the amide moiety ensures the synthetic utility of the Mannich adducts.

引用

页码：2391 / 2394

页数：4

共 50 条

[1] Direct Catalytic Asymmetric Mannich-Type Reaction of Thioamides
Suzuki, Yuta
Yazaki, Ryo
Kumagai, Naoya
Shibasaki, Masakatsu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (27) : 5026 - 5029
[2] Direct Catalytic Asymmetric Mannich-Type Reaction of α-Sulfanyl Lactones
Takechi, Sho
Kumagai, Naoya
Shibasaki, Masakatsu
ORGANIC LETTERS, 2013, 15 (11) : 2632 - 2635
[3] Direct Catalytic Asymmetric Mannich-Type Reaction of α- and β-Fluorinated Amides
Brewitz, Lennart
Arteaga, Fernando Arteaga
Yin, Liang
Alagiri, Kaliyamoorthy
Kumagai, Naoya
Shibasaki, Masakatsu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) : 15929 - 15939
[4] Direct Catalytic Asymmetric Vinylogous Mannich-Type Reaction of γ-Butenolides with Ketimines
Yin, Liang
Takada, Hisashi
Kumagai, Naoya
Shibasaki, Masakatsu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) : 7310 - 7313
[5] Direct Catalytic Asymmetric Mannich-type Reaction of ,-Unsaturated -Butyrolactam with Ketimines
Lin, Shaoquan
Kumagai, Naoya
Shibasaki, Masakatsu
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (10) : 3296 - 3299
[6] Catalytic Asymmetric Mannich-Type Reaction of α-Haloacetonitriles
Saito, Akira
Shibasaki, Masakatsu
ORGANIC LETTERS, 2024, 26 (36) : 7546 - 7550
[7] A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols
Trost, Barry M.
Terrell, Lamont R.
Journal of the American Chemical Society, 2003, 125 (02): : 338 - 339
[8] Direct Catalytic Asymmetric Mannich-Type Reaction of α-N3 Amide
Sun, Zhongdong
Weidner, Karin
Kumagai, Naoya
Shibasaki, Masakatsu
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (49) : 17574 - 17577
[9] A direct catalytic asymmetric Mannich-type reaction to syn-amino alcohols
Trost, BM
Terrell, LR
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (02) : 338 - 339
[10] α-Halo Amides as Competent Latent Enolates: Direct Catalytic Asymmetric Mannich-Type Reaction
Kumagai, Naoya (nkumagai@bikaken.or.jp), 1600, American Chemical Society (139):

← 1 2 3 4 5 →