A practical kinetic resolution of 4-acetyl[2.2]paracyclophane

被引：36

作者：

Dorizon, P

Martin, C

Daran, JC

Fiaud, JC

Kagan, HB ^{[1
]}

机构：

[1] Univ Paris 11, Lab Catalyse Mol, ESA 8075, Inst Chim Mol Orsay, F-91405 Orsay, France

[2] CNRS, Chim Coordinat Lab, UPR 8241, F-31077 Toulouse, France

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 18期

关键词：

D O I：

10.1016/S0957-4166(01)00452-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The kinetic resolution of 4-acetyl[2.2]paracyclophane has been realized by borane reduction in the presence of a CBS catalyst. The structure of the two diastereomeric alcohol products has been established, The ketone was recovered in more than 99% e.e. at 69% conversion. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：2625 / 2630

页数：6

相关论文

共 31 条

[1] SIR97:: a new tool for crystal structure determination and refinement [J].

Altomare, A ;

Burla, MC ;

Camalli, M ;

Cascarano, GL ;

Giacovazzo, C ;

Guagliardi, A ;

Moliterni, AGG ;

Polidori, G ;

Spagna, R .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119

[2]

[Anonymous], 1996, CAMERON

[3]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO

[4]

2-Z

[5]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[6] MACRO RINGS .12. STEREOCHEMICAL CONSEQUENCES OF STERIC COMPRESSION IN THE SMALLEST PARACYCLOPHANE [J].

CRAM, DJ ;

ALLINGER, NL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) :6289-6294

[7] CHEMOENZYMATIC SYNTHESIS OF 1,2-AMINO-ALCOHOLS AND 1,3-AMINO-ALCOHOLS AND THEIR USE IN THE ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE AND ANTI-ACETOPHENONE OXIME METHYL-ETHER WITH BORANE [J].

DIDIER, E ;

LOUBINOUX, B ;

TOMBO, GMR ;

RIHS, G .

TETRAHEDRON, 1991, 47 (27) :4941-4958

[8] The oxazaborolidine-borane reduction of ketones: Identification and reactivity of transient intermediates [J].

Douglas, AW ;

Tschaen, DM ;

Reamer, RA ;

Shi, YJ .

TETRAHEDRON-ASYMMETRY, 1996, 7 (05) :1303-1308

[9] PARTIAL RESOLUTION THROUGH CHIRAL SYNTHESIS USING A RACEMIC-MIXTURE [J].

ELBABA, S ;

POULIN, JC ;

KAGAN, HB .

TETRAHEDRON, 1984, 40 (21) :4275-4284

[10] ABSOLUTE CONFIGURATION AND CIRCULAR DICHROISM OF OPTICALLY ACTIVE (2.2)PARACYCLOPHANE DERIVATIVES [J].

FALK, H ;

REICHROH.P ;

SCHLOGL, K .

TETRAHEDRON, 1970, 26 (02) :511-&

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