Phosphine-oxide-catalyzed Enantioselective Cross-aldol Reactions of Aldehydes with Trichlorosilane as Lewis Acid Promoter

被引：1

作者：

Kotani, Shunsuke ^{[1
]}

Hanamure, Takuya ^{[1
]}

Mori, Yoshiki ^{[1
]}

Nakajima, Makoto ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 5-1 Oe Honmachi, Kumamoto 8620973, Japan

来源：

CHEMCATCHEM | 2020年 / 12卷 / 19期

关键词：

Aldol reaction; Enantioselectivity; Hypervalent silicon; Lewis base; Phosphine oxide; BASIC N-FORMAMIDE; ASYMMETRIC REDUCTION; STEREOSELECTIVE REDUCTION; AROMATIC KETIMINES; ORGANIC ACTIVATORS; ORGANOCATALYSTS; IMINES; EFFICIENT; KETONES; ADDITIONS;

D O I：

10.1002/cctc.202000914

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A hypervalent silicon complex between trichlorosilane and a chiral phosphine oxide acts as an effective Lewis acid mediator that successfully promotes highly enantioselective cross-aldol reactions between two aldehydes. The high yielding transformation is realized with the assistance of triisobutylamine, which does not decompose trichlorosilane but rather converts the aldol donor into the silyl enol ether that undergoes the enantioselective cross-aldol reaction with a second aldehyde in combination with the chiral phosphine oxide catalyst.

引用

页码：4780 / 4783

页数：4

共 50 条

[1] Chiral phosphoramide-catalyzed, enantioselective, directed cross-aldol reactions of aldehydes
Denmark, SE
Bui, T
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5439 - 5444
[2] The first direct and enantioselective cross-aldol reaction of aldehydes
Northrup, AB
MacMillan, DWC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (24) : 6798 - 6799
[3] Asymmetric Histidine-Catalyzed Cross-Aldol Reactions of Enolizable Aldehydes
Zanda, Matteo
SYNTHESIS-STUTTGART, 2010, (03): : A16 - A17
[4] Enantioselective cross aldol reactions of aldehydes
Slone, Chase
Vanness, Brandon
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[5] syn-selective and enantioselective direct cross-aldol reactions between aldehydes catalyzed by an axially chiral amino sulfonamide
Kano, Taichi
Yamaguchi, Yukako
Tanaka, Youhei
Maruoka, Keiji
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1738 - 1740
[6] Asymmetric cross-Aldol Reactions between Two Carbonyl Compounds Catalyzed by Chiral PhosPhine Oxides
Kotani, Shunsuke
Nakajima, Makoto
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (12) : 1163 - 1173
[7] Asymmetric bisprolinamide-catalyzed cross-aldol reaction of aldehydes
Xiong, Yan
Wang, Fei
Dong, Shunxi
Liu, Xiaohua
Feng, Xiaoming
SYNLETT, 2008, (01) : 73 - 76
[8] Asymmetric cross-aldol reactions between two carbonyl compounds catalyzed by chiral phosphine oxides
Kotani S.
Nakajima M.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2020, 78 (12): : 1163 - 1173
[9] Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by the chiral phosphine oxide BINAPO
Kotani, Shunsuke
Hashimoto, Shunichi
Nakajima, Makoto
SYNLETT, 2006, (07) : 1116 - 1118
[10] Phosphine Oxide Catalyzed, Tetrachlorosilane-Mediated Enantioselective Direct Aldol Reactions of Thioesters
Rossi, Sergio
Annunziata, Rita
Cozzi, Franco
Raimondi, Laura Maria
SYNTHESIS-STUTTGART, 2015, 47 (14): : 2113 - 2124

← 1 2 3 4 5 →