Asymmetric Mukaiyama Aldol Reaction of Nonactivated Ketones Catalyzed by allo-Threonine-Derived Oxazaborolidinone

被引：28

作者：

Adachi, Shinya ^{[1
]}

Harada, Toshiro ^{[1
]}

机构：

[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 21期

关键词：

D O I：

10.1021/ol802087u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Mukaiyama aldol reaction of nonactivated ketones is realized for the first time by using an oxazaborolidinone catalyst derived from O-benzoyl-N-tosyl-allo-threonine. By employing a dimethylsilyl ketene S,O-acetal as a nucleophile, a variety of acetophenone derivatives afford the corresponding tertiary beta-hydroxy carbonyl compounds with high enantioselectivity up to 98% ee.

引用

页码：4999 / 5001

页数：3

共 26 条

[11] Dimethylsilyl ketene acetal as a nucleophile in asymmetric Michael reaction: Enhanced enantioselectivity in oxazaborolidinone-catalyzed reaction
Harada, T
Adachi, S
Wang, XW
[J]. ORGANIC LETTERS, 2004, 6 (26) : 4877 - 4879
[12] Development of highly enantioselective oxazaborolidinone catalysts for the reactions of acyclic α,β-unsaturated ketones
Harada, Toshiro
Kusukawa, Takahiro
[J]. SYNLETT, 2007, (12) : 1823 - 1835
[13] Cu(I)-catalyzed reductive aldol cyclizations:: Diastereo- and enantioselective synthesis of β-hydroxylactones
Lam, HW
Joensuu, PM
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4225 - 4228
[14] Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions
Langner, M
Rémy, P
Bolm, C
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (21) : 6254 - 6265
[15] Liu J, 2008, J AM CHEM SOC, V130, P5654, DOI [10.1021/ja800839w, 10.1021/ja800839W]
[16] Catalytic and asymmetric vinylogous mukaiyama reactions on aliphatic ketones:: Formal asymmetric synthesis of taurospongin A
Moreau, X
Bazán-Tejeda, B
Campagne, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) : 7288 - 7289
[17] A new method for the catalytic aldol reaction to ketones
Oisaki, K
Suto, Y
Kanai, M
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) : 5644 - 5645
[18] Catalytic enantioselective alkylative aldol reaction:: Efficient multicomponent assembly of dialkylzincs, allenic esters, and ketones toward highly functionalized δ-lactones with tetrasubstituted chiral centers
Oisaki, Kounosuke
Zhao, Dongbo
Kanai, Motomu
Shibasaki, Masakatsu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) : 7439 - 7443
[19] Catalytic enantioselective aldol reaction to ketones
Oisaki, Kounosuke
Zhao, Dongbo
Kanai, Motomu
Shibasaki, Masakatsu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) : 7164 - 7165
[20] NEW CATALYSTS FOR THE ASYMMETRIC ALDOL REACTION - CHIRAL BORANES PREPARED FROM ALPHA,ALPHA-DISUBSTITUTED GLYCINE ARENESULFONAMIDES
PARMEE, ER
TEMPKIN, O
MASAMUNE, S
ABIKO, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9365 - 9366

← 1 2 3 →