Addition of Bu3SnLi to tert-butanesulfinimines as an efficient route to chiral, nonracemic α-aminoorganostannanes

被引:57
作者
Kells, KW [1 ]
Chong, JM [1 ]
机构
[1] Univ Waterloo, Dept Chem, Guelph Waterloo Ctr Grad Work Chem & Biochem, Waterloo, ON N2L 3G1, Canada
关键词
D O I
10.1021/ol035702i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of Bu3SnLi to tert-butanesulfinimines proceeds with high diastereoselectivities to provide the expected adducts in excellent yields and typically with dr = >99:1. These adducts are readily converted to enantiomerically enriched N-Boc-protected alpha-aminoorganostannanes with complete retention of configuration.
引用
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页码:4215 / 4218
页数:4
相关论文
共 39 条
[1]  
ALBRECHT H, 1993, SYNTHESIS-STUTTGART, P981
[2]  
ALBRECHT H, 1994, SYNTHESIS-STUTTGART, P770
[3]   A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide [J].
Barrow, JC ;
Ngo, PL ;
Pellicore, JM ;
Selnick, HG ;
Nantermet, PG .
TETRAHEDRON LETTERS, 2001, 42 (11) :2051-2054
[4]  
BAUDIN JB, 1995, B SOC CHIM FR, V132, P739
[5]   COMPLEX-INDUCED PROXIMITY EFFECTS - ENANTIOSELECTIVE SYNTHESES BASED ON ASYMMETRIC DEPROTONATIONS OF N-BOC-PYRROLIDINES [J].
BEAK, P ;
KERRICK, ST ;
WU, SD ;
CHU, JX .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3231-3239
[6]   ENANTIOMERICALLY ENRICHED TERT-BOC-PROTECTED ALPHA-AMINOORGANOLITHIUMS - PREPARATION AND CONFIGURATIONAL STABILITY [J].
CHONG, JM ;
PARK, SB .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2220-2222
[7]   Asymmetric synthesis of α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines [J].
Cogan, DA ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :268-269
[8]   Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].
Cogan, DA ;
Liu, GC ;
Ellman, J .
TETRAHEDRON, 1999, 55 (29) :8883-8904
[9]   Asymmetric synthesis of quaternary α-amino phosphonates using sulfinimines [J].
Davis, FA ;
Lee, S ;
Yan, HX ;
Titus, DD .
ORGANIC LETTERS, 2001, 3 (11) :1757-1760
[10]   Concise asymmetric synthesis of α-amino acid derivatives from N-sulfinylimino esters [J].
Davis, FA ;
McCoull, W .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3396-3397