Enantioselective borane reduction of aromatic ketones using chiral BINOL derivatives as ligands in an aluminum catalyst

被引：26

作者：

Lin, YM ^{[1
]}

Fu, IP ^{[1
]}

Uang, BJ ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(02)00008-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral aluminum complex-catalyzed asymmetric borane reduction of aromatic ketones has been successfully carried out in the presence of (R)-BINOL derivatives as ligands. Secondary alcohols were obtained in high yields with good enantioselectivities (up to 90% e.e.). (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3217 / 3221

页数：5

相关论文

共 33 条

[21] ASYMMETRIC REDUCTIONS WITH ORGANOBORANE REAGENTS [J].

MIDLAND, MM .

CHEMICAL REVIEWS, 1989, 89 (07) :1553-1561

[22] Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp: A predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation [J].

Naemura, K ;

Murata, M ;

Tanaka, R ;

Yano, M ;

Hirose, K ;

Tobe, Y .

TETRAHEDRON-ASYMMETRY, 1996, 7 (11) :3285-3294

[23] Asymmetric reduction of ketones by the acetone powder of Geotrichum candidum [J].

Nakamura, K ;

Matsuda, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) :8957-8964

[24] POLYMERIZATION OF ENANTIOMERICALLY PURE 2,3-DICARBOALKOXYNORBORNADIENES AND 5,6-DISUBSTITUTED NORBORNENES BY WELL-CHARACTERIZED MOLYBDENUM RING-OPENING METATHESIS POLYMERIZATION INITIATORS - DIRECT DETERMINATION OF TACTICITY IN CIS, HIGHLY TACTIC AND TRANS, HIGHLY TACTIC POLYMERS [J].

ODELL, R ;

MCCONVILLE, DH ;

HOFMEISTER, GE ;

SCHROCK, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3414-3423

[25] Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines [J].

Sato, S ;

Watanabe, H ;

Asami, M .

TETRAHEDRON-ASYMMETRY, 2000, 11 (21) :4329-4340

[26] A simple synthetic approach to 3,3′-diaryl BINOLs [J].

Simonsen, KB ;

Gothelf, KV ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7536-7538

[27]

SINGH VK, 1992, SYNTHESIS-STUTTGART, V605, P617

[28] HOST-GUEST COMPLEXATION .14. HOST COVALENTLY BOUND TO POLYSTYRENE RESIN FOR CHROMATOGRAPHIC RESOLUTION OF ENANTIOMERS OF AMINO-ACID AND ESTER SALTS [J].

SOGAH, GDY ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (11) :3035-3042

[29] A NEW PREPARATIVE METHOD FOR OPTICALLY-ACTIVE DIARYLCARBINOLS [J].

TODA, F ;

TANAKA, K ;

KOSHIRO, K .

TETRAHEDRON-ASYMMETRY, 1991, 2 (09) :873-874

[30] Highly efficient enantioselective synthesis of optically active dihydropyrones by chiral titanium(iv) (5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol) complexes [J].

Wang, B ;

Feng, XM ;

Cui, X ;

Liu, H ;

Jiang, YZ .

CHEMICAL COMMUNICATIONS, 2000, (17) :1605-1606

← 1 2 3 4 →