Catalytic Asymmetric Protonation of Chiral Calcium Enolates via 1,4-Addition of Malonates

被引：58

作者：

Poisson, Thomas

Yamashita, Yasuhiro

Kobayashi, Shu ^{[1
]}

机构：

[1] Univ Tokyo, Japan Sci & Technol Agcy, ERATO, HFRE Div,Sch Sci,Dept Chem,Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 23期

关键词：

SYNTHESEN MIT KETENEN; ALPHA-AMINO-ACIDS; ENANTIOSELECTIVE PROTONATION; 1,4-ADDITION/ENANTIOSELECTIVE PROTONATION; ORGANISCHE KATALYSATOREN; BETA(2)-AMINO ACIDS; CONJUGATE ADDITIONS; MICHAEL ADDITIONS; ATOM TRANSFER; COMPLEXES;

D O I：

10.1021/ja102555a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric protonation of chiral calcium enolates was performed. Chiral calcium enolates, prepared in situ from imides and malonates via 1,4-addition in the presence of catalytic amounts of Ca(OEt)(2), Ph-PyBox, and achiral phenol, were smoothly protonated to afford adducts bearing tertiary asymmetric carbons in high yields with high enantioselectivities. The adducts were readily converted to optically active 2-substituted 1,5-dicarboxylic acid derivatives.

引用

页码：7890 / +

页数：4

共 50 条

[41] STEREOCHEMISTRY IN THE PROTONATION OF ENOLATES GENERATED FROM 2-SUBSTITUTED 2-CYCLOPENTEN-1-ONES BY THE 1,4-ADDITION OF TRIALKYLSILYL AND TRIBUTYLSTANNYL ANIONS
KUSUDA, S
UENO, Y
TORU, T
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 97 (1-4): : 63 - 70
[42] On 1,2-and 1,4-addition I The 1,4-addition of potassium isocyanide
Michael, A
Weiner, N
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 : 744 - 753
[43] Organocatalytic Asymmetric 1,6-Addition/1,4-Addition Sequence to 2,4-Dienals for the Synthesis of Chiral Chromans
Poulsen, Pernille H.
Feu, Karla Santos
Paz, Bruno Matos
Jensen, Frank
Jorgensen, Karl Anker
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (28) : 8203 - 8207
[44] A Nickel-Diamine/Mesoporous Silica Composite as a Heterogeneous Chiral Catalyst for Asymmetric 1,4-Addition Reactions
Ishitani, Haruro
Kanai, Kan
Yoo, Woo-Jin
Yoshida, Tomoko
Kobayashi, Shu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (38) : 13313 - 13317
[45] 1,4-ADDITION TO CITRAL
SCHWARZ, M
WAKABAYASHI, N
THING, EG
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1979, 11 (02) : 97 - 99
[46] High performance of a chiral diene-rhodium catalyst for the asymmetric 1,4-addition of arylboroxines to α,β-unsaturated ketones
Chen, FX
Kina, A
Hayashi, T
ORGANIC LETTERS, 2006, 8 (02) : 341 - 344
[47] Rhodium-catalyzed asymmetric 1,4-addition of organometallic reagents
T. Hayashi
Russian Chemical Bulletin, 2003, 52 : 2595 - 2605
[48] Chiral tetrafluorobenzobarrelenes as highly efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids
Nishimura, Takahiro
Nagaosa, Makoto
Hayashi, Tamio
CHEMISTRY LETTERS, 2008, 37 (08) : 860 - 861
[49] Rhodium-catalyzed asymmetric 1,4-addition of organometallic reagents
Hayashi, T
RUSSIAN CHEMICAL BULLETIN, 2003, 52 (12) : 2595 - 2605
[50] Chiral Nanoparticles/Lewis Acids as Cooperative Catalysts for Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Amides
Yasukawa, Tomohiro
Saito, Yuuki
Miyamura, Hiroyuki
Kobayashi, Shu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (28) : 8058 - 8061

← 1 2 3 4 5 →