Amino acid mediated borane reduction of ketones

被引：0

作者：

Teodorovic, AV ^{[1
]}

Joksovic, MD

Konstantinovic, SK

Mojsilovic, BM

Mihailovic, ML

机构：

[1] Univ Kragujevac, Fac Sci, YU-34000 Kragujevac, Yugoslavia

[2] Univ Belgrade, Fac Sci, YU-11000 Belgrade, Yugoslavia

来源：

MONATSHEFTE FUR CHEMIE | 2000年 / 131卷 / 01期

关键词：

acetophenone; asymmetric induction; modified borane reduction; proline;

D O I：

10.1007/s007060050010

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Acetophenone, 2,2-dimethylcyclopentanone, 3,3-dimethyl-2-butanone, 3-methyl-2-butanone, and 2-pentanone were reduced with (S)-proline- and (S)-phenylalanine-mediated borane in good to very good yields giving predominantly (32-86% ee) alcohols of (R)-configuration.

引用

页码：91 / 95

页数：5

共 12 条

[1] RECENT ADVANCES IN ASYMMETRIC-SYNTHESIS .2. [J].

APSIMON, JW ;

COLLIER, TL .

TETRAHEDRON, 1986, 42 (19) :5157-5254

[2] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].

BLASER, HU .

CHEMICAL REVIEWS, 1992, 92 (05) :935-952

[3]

BROWN HC, 1975, ORGANIC SYNTHESES VI, pCH9

[4] ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANE, CATALYZED BY (S)-(-)-PROLINE OR (S)-(+)-PROLINOL [J].

BRUNEL, JM ;

MAFFEI, M ;

BUONO, G .

TETRAHEDRON-ASYMMETRY, 1993, 4 (10) :2255-2260

[5] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[6] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[7] ASYMMETRIC BORON-CATALYZED REACTIONS [J].

DELOUX, L ;

SREBNIK, M .

CHEMICAL REVIEWS, 1993, 93 (02) :763-784

[8] ASYMMETRIC-SYNTHESIS USING CHIRALLY MODIFIED BOROHYDRIDES .1. ENANTIOSELECTIVE REDUCTION OF AROMATIC KETONES WITH THE REAGENT PREPARED FROM BORANE AND (S)-VALINOL [J].

ITSUNO, S ;

HIRAO, A ;

NAKAHAMA, S ;

YAMAZAKI, N .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1673-1676

[9] COMPUTATIONAL ELUCIDATION OF THE CATALYTIC MECHANISM FOR KETONE REDUCTION BY AN OXAZABOROLIDINE-BORANE ADDUCT [J].

LINNEY, LP ;

SELF, CR ;

WILLIAMS, IH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (14) :1651-1652

[10]

SINGH VK, 1992, SYNTHESIS-STUTTGART, P605

← 1 2 →