Ni(II) Tol-BINAP-catalyzed enantioselective orthoester alkylations of N-acylthiazolidinethiones

被引：57

作者：

Evans, DA ^{[1
]}

Thomson, RJ ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 30期

关键词：

D O I：

10.1021/ja053386s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of a Ni(II) (S)-Tol-BINAP-catalyzed enantioselective alkylation of N-acylthiazolidinethiones with trimethyl orthoformate is described. The reaction is general with respect to the thiazolidinethione, providing the desired adducts in good to excellent yield and with high levels of enantioselectivity (11 examples, 51-92% yield, 90-99% ee). The products are readily converted into a variety of synthetically useful derivatives in a straightforward manner. Copyright © 2005 American Chemical Society.

引用

页码：10506 / 10507

页数：2

共 18 条

[11] The SAMP-/RAMP-hydrazone methodology in asymmetric synthesis [J].

Job, A ;

Janeck, CF ;

Bettray, W ;

Peters, R ;

Enders, D .

TETRAHEDRON, 2002, 58 (12) :2253-+

[12]

Meyers A. I., 1983, ASYMMETRIC SYNTHESIS, V3, P213

[13] 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

[14] Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones [J].

Myers, AG ;

Yang, BH ;

Chen, H ;

McKinstry, L ;

Kopecky, DJ ;

Gleason, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (28) :6496-6511

[15] ASYMMETRIC ALKYLATION OF NORMAL-ACYLSULTAMS - A GENERAL-ROUTE TO ENANTIOMERICALLY PURE, CRYSTALLINE C(ALPHA,ALPHA)-DISUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

OPPOLZER, W ;

MORETTI, R ;

THOMI, S .

TETRAHEDRON LETTERS, 1989, 30 (41) :5603-5606

[16] Superacidity and superelectrophilicity of BF3-carbonyl complexes [J].

Ren, JH ;

Cramer, CJ ;

Squires, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2633-2634

[17] Versatile asymmetric synthesis of the kavalactones: First synthesis of (+)-kavain [J].

Smith, TE ;

Djang, M ;

Velander, AJ ;

Downey, CW ;

Carroll, KA ;

van Alphen, S .

ORGANIC LETTERS, 2004, 6 (14) :2317-2320

[18] Preparation, crystal structure analysis, and catalytic application of [(S)-BINAP]Ni(COD) and [(S)-BINAP]NiBr2 [J].

Spielvogel, DJ ;

Davis, WM ;

Buchwald, SL .

ORGANOMETALLICS, 2002, 21 (18) :3833-3836

← 1 2 →