Palladium-catalyzed highly regio- and stereoselective carbon-carbon bond formation reaction of γ-substituted vinylaziridines with a silylated masked acyl cyanide reagent

被引:11
作者
Kawamura, Tomoyuki [1 ]
Matsu, Nanae [2 ]
Yamauchi, Daisuke [1 ]
Tanabe, Yoo [2 ]
Nemoto, Hisao [1 ]
机构
[1] Univ Tokushima, Grad Sch, Div Heath Biosci, Dept Pharmaceut Chem, Tokushima 7708505, Japan
[2] Kwansei Gakuin Univ, Sch Sci & Technol, Dept Chem, Sanda 6691337, Japan
关键词
Palladium; Aziridine; pi-Allyl complex; Masked acyl cyanide; RING-OPENING REACTIONS; BETA-SUBSTITUENTS; ACID; PRONUCLEOPHILES; ALLYLATION; COMPLEXES; BEARING; ALPHA;
D O I
10.1016/j.tet.2013.04.129
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly regio- and stereoselective carbon-carbon bond formation reaction of vinylaziridines using a masked acyl cyanide reagent possessing a tert-butyldimethylsilyl group occurred in the presence of a catalytic amount of palladium complex in excellent yield. It is considered that these excellent selectivities are the result of three simultaneous conditions, strained leaving group, small nucleophile, and ligand with small cone-angle. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5331 / 5341
页数:11
相关论文
共 32 条
[1]   Cone angles:: Tolman's and Plato's [J].
Bunten, KA ;
Chen, LZ ;
Fernandez, AL ;
Poë, AJ .
COORDINATION CHEMISTRY REVIEWS, 2002, 233 :41-51
[2]  
Cantrill AA, 1996, SYNLETT, P847
[3]  
Davies J. A., 1995, COMPREHENSIVE ORGANO, V9
[4]  
Godleski S. A., 1991, COMPREHENSIVE ORGANI, V4
[5]   SYN-S(N)2' PATHWAY IN THE REACTION OF CERTAIN GAMMA-(MESYLOXY) ALPHA, BETA-ENOATES WITH RCU(CN)MGX.BF3 REAGENTS - IMPORTANCE OF MGX AND BULKY R-GROUP UPON THE DIASTEREOSELECTIVITY [J].
IBUKA, T ;
TAGA, T ;
HABASHITA, H ;
NAKAI, K ;
TAMAMURA, H ;
FUJII, N ;
CHOUNAN, Y ;
NEMOTO, H ;
YAMAMOTO, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1207-1214
[6]   Palladium acetic acid catalyzed allylation of some pronucleophiles with simple alkynes [J].
Kadota, I ;
Shibuya, A ;
Gyoung, YS ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) :10262-10263
[7]   RUTHENIUM-CATALYZED ALDOL AND MICHAEL REACTIONS OF ACTIVATED NITRILES [J].
NAOTA, T ;
TAKI, H ;
MIZUNO, M ;
MURAHASHI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (15) :5954-5955
[8]   A three-step preparation of MAC reagents from malononitrile [J].
Nemoto, H ;
Li, XM ;
Ma, RJ ;
Suzuki, I ;
Shibuya, M .
TETRAHEDRON LETTERS, 2003, 44 (01) :73-75
[9]   Synthesis of optically active phenylglycine derivatives from Ss-(+)-N-(benzylidene)-p-toluenesulfinamide by using Lewis acids and tert-amines [J].
Nemoto, H ;
Ma, RJ ;
Moriguchi, H ;
Suzuki, I ;
Shibuya, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 611 (1-2) :445-448
[10]   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