Convenient synthesis of optically active 1,2-diol monosulfonates and terminal epoxides via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones

被引：29

作者：

Cho, BT ^{[1
]}

Yang, WK ^{[1
]}

Choi, OK ^{[1
]}

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 10期

关键词：

D O I：

10.1039/b010155i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very convenient asymmetric synthesis of 1,2-diol monosulfonates and terminal epoxides with high optical purity via oxazaborolidine-catalyzed asymmetric borane reduction of alpha -sulfonyloxy ketones using N-ethyl-N-isopropylaniline-borane complex as borane carrier has been developed.

引用

页码：1204 / 1211

页数：8

共 79 条

[61]

NUBO Y, 1991, SYNLETT, P97

[62] A simple and efficient method for the preparation of homochiral amines: Application to the synthesis of a new C-2 symmetric triamine [J].

OBrien, P ;

Poumellec, P .

TETRAHEDRON LETTERS, 1996, 37 (31) :5619-5622

[63] HIGHLY ENANTIOSELECTIVE, LOW-TEMPERATURE EPOXIDATION OF STYRENE [J].

PALUCKI, M ;

POSPISIL, PJ ;

ZHANG, W ;

JACOBSEN, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9333-9334

[64] Microbiological transformations .33. Fungal epoxide hydrolases applied to the synthesis of enantiopure para-substituted styrene oxides. A mechanistic approach [J].

PedragosaMoreau, S ;

Morisseau, C ;

Zylber, J ;

Archelas, A ;

Baratti, J ;

Furstoss, R .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7402-7407

[65] Microbiological transformations .37. An enantioconvergent synthesis of the beta-blocker (R)-Nifenalol(R) using a combined chemoenzymatic approach [J].

PedragosaMoreau, S ;

Morisseau, C ;

Baratti, J ;

Zylber, J ;

Archelas, A ;

Furstoss, R .

TETRAHEDRON, 1997, 53 (28) :9707-9714

[66] A COMBINED SYNTHETIC AND AB-INITIO STUDY OF CHIRAL OXAZABOROLIDINES STRUCTURE AND ENANTIOSELECTIVITY RELATIONSHIPS [J].

QUALLICH, GJ ;

BLAKE, JF ;

WOODALL, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) :8516-8525

[67] Convenient synthesis of (+/-)- and (S)-antipode of (4E,7S)-7-methoxytetradec-4-enoic acid, the antimicrobial principle of marine cyanophyte [J].

Sankaranarayanan, S ;

Sharma, A ;

Chattopadhyay, S .

TETRAHEDRON-ASYMMETRY, 1996, 7 (09) :2639-2643

[68] A 2-STEP ASYMMETRIC-SYNTHESIS OF (R)-MONOARYL EPOXIDES USING A CHIRAL OXATHIANE AS A RECOVERABLE REAGENT - APPLICATION TO THE PREPARATION OF (R)-BETA-ADRENERGIC COMPOUNDS [J].

SOLLADIECAVALLO, A ;

DIEPVOHUULE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) :3494-3498

[69] Enantioselectivity of a recombinant epoxide hydrolase from Agrobacterium radiobacter [J].

Spelberg, JHL ;

Rink, R ;

Kellogg, RM ;

Janssen, DB .

TETRAHEDRON-ASYMMETRY, 1998, 9 (03) :459-466

[70] A practical synthesis of (R)-3-chlorostyrene oxide starting from 3-chloroethylbenzene [J].

Tanaka, K ;

Yasuda, M .

TETRAHEDRON-ASYMMETRY, 1998, 9 (18) :3275-3282

← 1 2 3 4 5 6 7 8 →