ENANTIOSELECTIVE 1,2-ADDITION OF GRIGNARD-REAGENTS TO ALDEHYDES USING CHIRAL DIAMINES

被引:36
作者
NAKAJIMA, M [1 ]
TOMIOKA, K [1 ]
KOGA, K [1 ]
机构
[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/S0040-4020(01)80177-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective 1,2-addition of Grignard reagents to aldehydes using chiral diamine 1, 2 was examined. High ee (up to 75%) of carbinol was achieved by the reaction of arylmagnesium bromide and benzaldehyde with chiral diamine. Utilizing 2,4,6-trimethylphenoxyaluminum dichloride 6 as a coordinating agent to benzaldehyde, enantioselectivity of the addition of alkylmagnesium bromide was dramatically increased (up to 70%).
引用
收藏
页码:9751 / 9758
页数:8
相关论文
共 36 条
[1]   ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS IN THE PRESENCE OF CHIRAL LIGANDS [J].
COLOMBO, L ;
GENNARI, C ;
POLI, G ;
SCOLASTICO, C .
TETRAHEDRON, 1982, 38 (17) :2725-2727
[2]  
DRADI E, 1980, GAZZ CHIM ITAL, V110, P353
[3]   CHIRAL TITANIUM COMPLEXES FOR ENANTIOSELECTIVE ADDITION OF NUCLEOPHILES TO CARBONYL GROUPS [J].
DUTHALER, RO ;
HAFNER, A .
CHEMICAL REVIEWS, 1992, 92 (05) :807-832
[4]   ENANTIOSELECTIVE ADDITION OF N-BUTYLLITHIUM TO BENZALDEHYDE IN THE PRESENCE OF CHIRAL LITHIUM AMIDES [J].
ELEVELD, MB ;
HOGEVEEN, H .
TETRAHEDRON LETTERS, 1984, 25 (45) :5187-5190
[5]   SIGNIFICANCE OF HALIDE IN GRIGNARD REAGENTS [J].
FRENCH, W ;
WRIGHT, GF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1964, 42 (11) :2474-&
[6]   EU(FOD) 3-SHIFTED H-2-NMR AS A PROBE OF CHIRALITY DUE TO DEUTERIUM SUBSTITUTION - STEREOSPECIFIC DEUTERIUM INCORPORATION INTO 2-N-HEXYL-5-N-PROPYLRESORCINOL - A POLYKETIDE PRODUCED BY PSEUDOMONUS SP B-9004 [J].
FURUKAWA, J ;
IWASAKI, S ;
OKUDA, S .
TETRAHEDRON LETTERS, 1983, 24 (47) :5261-5264
[7]  
INCH TD, 1969, TETRAHEDRON LETT, P3657
[8]   ASYMMETRIC REDUCTIONS .7. THE ACTION OF THE GRIGNARD REAGENT FROM (+)-1-CHLORO-2-METHYLBUTANE ON A SERIES OF ALKYL PHENYL KETONES [J].
MACLEOD, R ;
WELCH, FJ ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (04) :876-880
[9]   ORGANOALUMINUMS IN ORGANIC-SYNTHESIS [J].
MARUOKA, K ;
YAMAMOTO, H .
TETRAHEDRON, 1988, 44 (16) :5001-5032
[10]   CHIRAL CATALYSIS OF ADDITIONS OF ALKYLLITHIUMS TO ALDEHYDES [J].
MAZALEYRAT, JP ;
CRAM, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4585-4586