MIB: an advantageous alternative to DAIB for the addition of organozinc reagents to aldehydes

被引:142
作者
Nugent, WA [1 ]
机构
[1] DuPont Co Inc, Cent Res & Dev, Wilmington, DE 19880 USA
关键词
D O I
10.1039/a904042k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3-exo-Morpholinoisoborneol (MIB) catalyzes the addition of organozinc reagents to aldehydes in high enantiomeric excess and provides several advantages over the venerable amino alcohol ligand DAIB.
引用
收藏
页码:1369 / 1370
页数:2
相关论文
共 21 条
[1]   Novel ligands derived from S-tyrosine for the enantioselective addition of diethylzinc to aldehydes [J].
Beliczey, J ;
Giffels, G ;
Kragl, U ;
Wandrey, C .
TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1529-1530
[2]   AMINOBICYCLO2,2,1!HEPTANES .2. DIASTEREOISOMERIC DIMETHYLAMINOBORNYL ACETATES [J].
CHITTENDEN, RA ;
COOPER, GH .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (01) :49-+
[3]   ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES CATALYZED BY CHIRAL NI(II) AMINOALCOHOL COMPLEXES [J].
DEVRIES, AHM ;
JANSEN, JFGA ;
FERINGA, BL .
TETRAHEDRON, 1994, 50 (15) :4479-4491
[4]   Catalytic asymmetric addition of ZnPh2 to ketones:: Enantioselective formation of quaternary stereocenters [J].
Dosa, PI ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :445-446
[5]  
Grignard V, 1900, CR HEBD ACAD SCI, V130, P1322
[6]   Quantitative analysis of the chiral amplification in the amino alcohol-promoted asymmetric alkylation of aldehydes with dialkylzincs [J].
Kitamura, M ;
Suga, S ;
Oka, H ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (38) :9800-9809
[7]   ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES PROMOTED BY CHIRAL AMINO-ALCOHOLS - MECHANISM AND NONLINEAR EFFECT [J].
KITAMURA, M ;
OKADA, S ;
SUGA, S ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4028-4036
[8]   CATALYTIC ASYMMETRIC INDUCTION - HIGHLY ENANTIOSELECTIVE ADDITION OF DIALKYLZINCS TO ALDEHYDES [J].
KITAMURA, M ;
SUGA, S ;
KAWAI, K ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) :6071-6072
[9]   Lipase-catalyzed transesterification of aryl-substituted alkanols in an organic solvent [J].
Nakamura, K ;
Kawasaki, M ;
Ohno, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (04) :1079-1085
[10]  
Noyori R., 1994, ASYMMETRIC CATALYSIS