A NOVEL STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF TRANS-9-ALKYL-2-BENZYL-5-METHYL-6,7-BENZOMORPHANS

被引：4

作者：

DEHGHANI, A

BAI, X

MASCARELLA, SW

BOWEN, WD

CARROLL, FI

机构：

[1] RES TRIANGLE INST,RES TRIANGLE PK,NC 27709

[2] NIDDK,MED CHEM LAB,BETHESDA,MD 20892

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 48期

关键词：

D O I：

10.1016/0040-4039(94)88402-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first stereo- and enantioselective syntheses of trans-9-alkyl-2-benzyl-5-methyl-6,7-benzo- morphans (12) are described. The addition of alkyl magnesium halides to (R)-2-naphthyl-4-phenyl-1,3-oxazolidine (7) followed by treatment with iodomethane and quenching with acid gave (1S,2S)-2-alkyl-1-methyl-1,2-dihydronaphthalenecarboxaldehyde (10). Homologation of 10 followed by reductive amination using benzylamine gave (1S,2S)-trans-2-alkyl-1-benzylaminoethyl-1-methyl-1,2-dihydronaphthalene (11). Mercuric acetate-assisted cyclization of 11 followed by LAK reduction afforded (1S,5S,9R)-12.

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页码：8969 / 8972

页数：4

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