Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates

被引：179

作者：

Evans, DA ^{[1
]}

Downey, CW ^{[1
]}

Hubbs, JL ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 29期

关键词：

D O I：

10.1021/ja035509j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective aldol reaction of N-propionylthiazolidinethione and representative aldehydes is disclosed. The reaction is catalyzed by [Ni(S,S)-t-BuBox](Otf)2. Enolization is effected by 2,6-lutidine, and TMSOTf facilitates catalyst turnover. Syn diastereoselectivities range from 88:12 to 97:3, and enantioselectivities are 90% or greater. Both aromatic and enolizable aliphatic aldehydes are included within the scope of this aldol addition process. Copyright © 2003 American Chemical Society.

引用

页码：8706 / 8707

页数：2

共 15 条

[1] Titanium enolates of thiazolidinethione chiral auxiliaries: Versatile tools for asymmetric aldol additions [J].

Crimmins, MT ;

Chaudhary, K .

ORGANIC LETTERS, 2000, 2 (06) :775-777

[2] Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones [J].

Evans, DA ;

Downey, CW ;

Shaw, JT ;

Tedrow, JS .

ORGANIC LETTERS, 2002, 4 (07) :1127-1130

[3] Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones [J].

Evans, DA ;

Tedrow, JS ;

Shaw, JT ;

Downey, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :392-393

[4] An improved procedure for the preparation of 2,2-bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-butylbis(oxazoline)] and derived copper(II) complexes [J].

Evans, DA ;

Peterson, GS ;

Johnson, JS ;

Barnes, DM ;

Campos, KR ;

Woerpel, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) :4541-4544

[5] THE USE OF CYSTEINE-DERIVED AND SERINE-DERIVED THIAZOLIDINETHIONES AND OXAZOLIDINETHIONES AS EFFICIENT CHIRAL AUXILIARIES IN ALDOL CONDENSATIONS [J].

HSIAO, CN ;

LIU, L ;

MILLER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (11) :2201-2206

[6] Enantioselective Michael additions of nitromethane by a catalytic double activation method using chiral Lewis acid and achiral amine catalysts [J].

Itoh, K ;

Kanemasa, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13394-13395

[7] Highly endo- and enantioselective asymmetric nitrone cycloadditions catalyzed by the aqua complex of 4,6-dibenzofurandiyl-2,2′-bis (4-phenyl-oxazoline)-nickel(II) perchlorate.: Transition structure based on dramatic effect of MS 4A on selectivities [J].

Kanemasa, S ;

Oderaotoshi, Y ;

Tanaka, J ;

Wada, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) :12355-12356

[8] Direct catalytic enantio- and diastereoselective aldol reaction using a Zn-Zn-linked-BINOL complex:: A practical synthesis of syn-1,2-diols [J].

Kumagai, N ;

Matsunaga, S ;

Yoshikawa, N ;

Ohshima, T ;

Shibasaki, M .

ORGANIC LETTERS, 2001, 3 (10) :1539-1542

[9] STANNOUS TRIFLATE MEDIATED ALDOL REACTION OF 3-ACYLTHIAZOLIDINE-2-THIONE - A CONVENIENT METHOD FOR THE STEREOSELECTIVE SYNTHESES OF BETA-HYDROXY ALDEHYDE AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES [J].

MUKAIYAMA, T ;

IWASAWA, N .

CHEMISTRY LETTERS, 1982, (12) :1903-1906

[10] NEW C4-CHIRAL 1,3-THIAZOLIDINE-2-THIONES - EXCELLENT CHIRAL AUXILIARIES FOR HIGHLY DIASTEREOCONTROLLED ALDOL-TYPE REACTIONS OF ACETIC-ACID AND ALPHA,BETA-UNSATURATED ALDEHYDES [J].

NAGAO, Y ;

HAGIWARA, Y ;

KUMAGAI, T ;

OCHIAI, M ;

INOUE, T ;

HASHIMOTO, K ;

FUJITA, E .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2391-2393

← 1 2 →