ENANTIOFACE DIFFERENTIATING REDUCTION OF KETO ACID IN THE PRESENCE OF 6-DEOXY-6-AMINO-BETA-CYCLODEXTRIN WITH NABH4 IN AQUEOUS-MEDIA

被引：21

作者：

HATTORI, K

TAKAHASHI, K

SAKAI, N

机构：

[1] Department of Industrial Chemistry, Faculty of Engineering, Tokyo Institute of Polytechnics, Atsugi, Kanagawa

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1992年 / 65卷 / 10期

关键词：

D O I：

10.1246/bcsj.65.2690

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The formation of an inclusion compound and the interaction of both ionic and hydrogen bonding were shown to be indispensable in the asymmetric reduction of keto acid in the presence of 6-deoxy-6-amino-beta-cyclodextrin with NaBH4 in an aqueous buffer solution. Furthermore, multiple interactions were elucidated and the enantioface differentiating reduction was induced in the concerted interactions. A mechanistic scheme for the enantioface differentiating attack of a reducing-reagent on the included substrate was suggested.

引用

页码：2690 / 2696

页数：7

共 19 条

[1]

ATWOOD JL, 1984, INCLUSION COMPOUNDS, V2

[2]

BABA N, 1978, TETRAHEDRON LETT, V44, P4281

[3]

Bender M. L., 1978, CYCLODEXTRIN CHEM, DOI [10.1007/978-3-642-66842-5, DOI 10.1007/978-3-642-66842-5]

[4] HOST-GUEST CHEMISTRY [J].

CRAM, DJ ;

CRAM, JM .

SCIENCE, 1974, 183 (4127) :803-809

[5]

CYMERMANCRAIG J, 1958, AUST J CHEM, V9, P222

[6] ASYMMETRIC REDUCTIONS BY NABH4 OF KETONE BETA-CYCLODEXTRIN COMPLEXES [J].

FORNASIER, R ;

RENIERO, F ;

SCRIMIN, P ;

TONELLATO, U .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (17) :3209-3211

[7] MULTIPLE INTERACTIONS BETWEEN HOST CYCLODEXTRIN AND GUEST COMPOUND ASSISTING ASYMMETRICALLY SELECTIVE REDUCTION WITH NABH4 IN AQUEOUS-MEDIA [J].

HATTORI, K ;

TAKAHASHI, K ;

UEMATSU, M ;

SAKAI, N .

CHEMISTRY LETTERS, 1990, (08) :1463-1466

[8]

HIRAOKA M, 1978, CROWN COMPOUNDS THEI, P249

[9]

KINOSHITA T, 1974, CHEM PHARM BULL, V22, P2735

[10] SYNTHESIS OF MONOSUBSTITUTED CYCLOHEXAAMYLOSES [J].

MELTON, LD ;

SLESSOR, KN .

CARBOHYDRATE RESEARCH, 1971, 18 (01) :29-+

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