Synthesis of optically active phenylglycine derivatives from Ss-(+)-N-(benzylidene)-p-toluenesulfinamide by using Lewis acids and tert-amines

被引：27

作者：

Nemoto, H ^{[1
]}

Ma, RJ ^{[1
]}

Moriguchi, H ^{[1
]}

Suzuki, I ^{[1
]}

Shibuya, M ^{[1
]}

机构：

[1] Univ Tokushima, Fac Pharmaceut Sci, Tokushima 7708505, Japan

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2000年 / 611卷 / 1-2期

关键词：

acyl cyanides; asymmetric synthesis; phenylglycine; amino acids and peptides; peptides; sulfinimines; Lewis acids;

D O I：

10.1016/S0022-328X(00)00478-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Stereoselective synthesis of L- and D-phenylglycine derivatives was accomplished by the reaction of Ss-(+)-N-(benzylidene)-p-toluenesulfinamide with 2-(tert-butyldimethylsiloxy)malononitrile (H-MAC-TBS) in the presence of Lewis acids and tert-amines. (C) 2000 Published by Elsevier Science S.A. All rights reserved.

引用

页码：445 / 448

页数：4

共 12 条

[1] Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides) [J].

Davis, FA ;

Reddy, RE ;

Szewczyk, JM ;

Reddy, GV ;

Portonovo, PS ;

Zhang, HM ;

Fanelli, D ;

Reddy, RT ;

Zhou, P ;

Carroll, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2555-2563

[2] N-SUBSTITUTED AND 2-SUBSTITUTED N-(PHENYLSULFONYL)GLYCINES AS INHIBITORS OF RAT LENS ALDOSE REDUCTASE [J].

DERUITER, J ;

BORNE, RF ;

MAYFIELD, CA .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (01) :145-151

[3] Catalytic in situ generation of Zn(II)-alkynilides under mild conditions:: A novel C=N addition process utilizing terminal acetylenes [J].

Frantz, DE ;

Fässler, R ;

Carreira, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11245-11246

[4]

NEMOTO H, 1994, TETRAHEDRON LETT, V35, P7785, DOI 10.1016/S0040-4039(00)77372-2

[5] PALLADIUM-CATALYZED ADDITION OF MASKED FORMYL CYANIDES ROCH(CN)(2) TO ALDEHYDES [J].

NEMOTO, H ;

KUBOTA, Y ;

YAMAMOTO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (14) :1665-1666

[6] DEVELOPMENT OF A NEW ACYL ANION EQUIVALENT FOR THE PREPARATION OF MASKED ACTIVATED ESTERS AND THEIR USE TO PREPARE A DIPEPTIDE [J].

NEMOTO, H ;

KUBOTA, Y ;

YAMAMOTO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4515-4516

[7]

NEMOTO H, 1993, SYNLETT, P465

[8] Stereoselective synthesis of alkenylated malonic diamide using masked acyl cyanide [J].

Nemoto, H ;

Ibaragi, T ;

Bando, M ;

Kido, M ;

Shibuya, M .

TETRAHEDRON LETTERS, 1999, 40 (07) :1319-1322

[9]

NEMOTO H, 1993, UNPUB

[10] Tin- or magnesium-mediated diastereoselective aldol-type reactions for the asymmetric synthesis of α-substituted serines [J].

Sano, S ;

Miwa, T ;

Liu, XK ;

Ishii, T ;

Takehisa, T ;

Shiro, M ;

Nagao, Y .

TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3615-3618

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