Stereoselective synthesis of 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-1,4-oxazine

被引：8

作者：

Ashwood, MS

Cottrell, IF

Davies, AJ

机构：

[1] Merck Sharp and Dohme Res. Labs., Hoddesdon, Hertfordshire EN11 9BU, Hertford Road

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(97)00058-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A convenient process for the preparation of the secondary amine 6, 2-(S)-(3,5-bis(trifluoromethyl)benzyloxy)-3-(S)-phenyl-1,4-oxazine, is described starting from the readily available (S)-phenylglycine 1. The process features efficient construction of the homochiral oxazinone intermediate 3 and stereoselective introduction of the 2-(3,5-bis(trifluoromethyl)-benzyloxy) group by L-Selectride reduction followed by in situ alkylation with the highly reactive 3,5-bis(trifluoromethyl)-benzyl triflate 4. (C) 1997 Elsevier Science Ltd.

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页码：957 / 963

页数：7

相关论文

共 9 条

[1] ASYMMETRIC-SYNTHESIS OF N-METHYL-ALPHA-AMINO ESTERS FROM A GLYOXAL DERIVED CHIRAL HETEROCYCLE [J].

AGAMI, C ;

COUTY, F ;

PRINCE, B ;

PUCHOT, C .

TETRAHEDRON, 1991, 47 (25) :4343-4354

[2] LITHIUM TRI-SEC-BUTYLBOROHYDRIDE - NEW REAGENT FOR REDUCTION OF CYCLIC AND BICYCLIC KETONES WITH SUPER STEREOSELECTIVITY - REMARKABLY SIMPLE AND PRACTICAL PROCEDURE FOR CONVERSION OF KETONES TO ALCOHOLS IN EXCEPTIONALLY HIGH STEREOCHEMICAL PURITY [J].

BROWN, HC ;

KRISHNAMURTHY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7159-+

[3] SYNTHESIS, STRUCTURE END REACTIONS OF CHIRAL OXAZINONES DERIVED FROM L-EPHEDRINE [J].

CHANG, CJ ;

FANG, JM ;

LEE, GH ;

WANG, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (24) :3587-3593

[4] UBER DIE OPTISCHE REINHEIT UND DIE CHIRALITAT DER ENANTIOMEREN ALPHA-2H1-BENZYLAMINE [J].

GERLACH, H .

HELVETICA CHIMICA ACTA, 1966, 49 (08) :2481-&

[5] 2(S)-((3,5-bis(trifluoromethyl)benzyl)oxy)-3(S)-phenyl-4-((3-oxo-1,2,4-triazol-5-yl)methyl)morpholine .1. A potent, orally active, morpholine-based human neurokinin-1 receptor antagonist [J].

Hale, JJ ;

Mills, SG ;

MacCoss, M ;

Shah, SK ;

Qi, HB ;

Mathre, DJ ;

Cascieri, MA ;

Sadowski, S ;

Strader, CD ;

MacIntyre, DE ;

Metzger, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (09) :1760-1762

[6] PREPARATION OF SOME NEW DERIVATIVES OF MORPHOL-2-ONE [J].

JANKOWSKI, K ;

BERSE, C .

CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1968, 46 (11) :1939-+

[7] SYNTHESIS AND REACTION OF OPTICALLY-ACTIVE MORPHOLINONES [J].

KASHIMA, C ;

HARADA, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1521-1526

[8]

STANG PJ, 1980, SYNTHESIS-STUTTGART, P283

[9] PRACTICAL ASYMMETRIC SYNTHESES OF ALPHA-AMINO-ACIDS THROUGH CARBON CARBON BOND CONSTRUCTIONS ON ELECTROPHILIC GLYCINE TEMPLATES [J].

WILLIAMS, RM ;

SINCLAIR, PJ ;

ZHAI, D ;

CHEN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1547-1557