A convenient synthesis of (1S,2R)-1,2-indene oxide and trans-(1S,2S)-2-bromo-1-indanol via oxazaborolidine-catalyzed borane reduction

被引：17

作者：

Choi, OK ^{[1
]}

Cho, BT ^{[1
]}

机构：

[1] Hallym Univ, Dept Chem, Kangwondo 200702, South Korea

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(01)00151-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A facile synthesis of (1S,2R)-indene oxide with > 99% e.e. and (1S,2S)-trans-2-bromo-1-indanol with 87% e.e. has been established by employing CBS-oxazaborolidine-catalyzed asymmetric borane reduction of 2-p-toluenesulfonyloxy-1-indanone using N-ethyl-N-isoyropylaniline-borane complex as the borane carrier. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：903 / 907

页数：5

相关论文

共 24 条

[1] On the baker's yeast mediated transformation of α-bromoenones.: Synthesis of (1S,2R)-2-bromoindan-1-ol and (2S,3S)-3-bromo-4-phenylbutan-2-ol [J].

Aleu, J ;

Fronza, G ;

Fuganti, C ;

Perozzo, V ;

Serra, S .

TETRAHEDRON-ASYMMETRY, 1998, 9 (09) :1589-1596

[2] SYNTHESIS OF DEOXYHALOGENO SUGARS - DISPLACEMENT OF THE (TRIFLUOROMETHANESULFONYL)OXY (TRIFLYL) GROUP BY HALIDE ION [J].

BINKLEY, RW ;

AMBROSE, MG ;

HEHEMANN, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (22) :4387-4391

[3] CHEMICAL SYNTHESIS AND OPTICAL PURITY DETERMINATION OF OPTICALLY-ACTIVE 1,2-EPOXYINDAN AND ALCOHOL PRODUCTS WHICH ARE ALSO DERIVED FROM MAMMALIAN OR MICROBIAL-METABOLISM OF INDENE OR INDANONES [J].

BOYD, DR ;

SHARMA, ND ;

SMITH, AE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (11) :2767-2770

[4] Stereoselective dioxygenase-catalysed benzylic hydroxylation at prochiral methylene groups in the chemoenzymatic synthesis of enantiopure vicinal aminoindanols. [J].

Boyd, DR ;

Sharma, ND ;

Bowers, NI ;

Goodrich, PA ;

Groocock, MR ;

Blacker, AJ ;

Clarke, DA ;

Howard, T ;

Dalton, H .

TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1559-1562

[5] INVESTIGATION OF METHODS FOR PREPARING PURE SECONDARY ALKYL HALIDES [J].

CASON, J ;

CORREIA, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (10) :3645-&

[6] Catalytic enantioselective reactions.: Part 16.: Oxazaborolidine-catalyzed asymmetric borane reduction of α-keto acetals [J].

Cho, BT ;

Chun, YS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (15) :2095-2100

[7] A practical method for synthesis of terminal 1,2-diols in high enantiomeric excess via oxazaborolidine-catalyzed asymmetric reduction [J].

Cho, BT ;

Chun, YS .

TETRAHEDRON-ASYMMETRY, 1999, 10 (10) :1843-1846

[8] An efficient synthesis of enantiopure 3-chlorostyrene oxide via oxazaborolidine-catalyzed reduction [J].

Choi, OK ;

Cho, BT .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2000, 32 (05) :493-497

[9]

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

[10]

2-Z