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

Authors
DEHGHANI A BAI X MASCARELLA SW BOWEN WD CARROLL FI
Citation
A. Dehghani et al., A NOVEL STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF TRANS-9-ALKYL-2-BENZYL-5-METHYL-6,7-BENZOMORPHANS, Tetrahedron letters, 35(48), 1994, pp. 8969-8972
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
48
Year of publication
1994
Pages
8969 - 8972
Database
ISI
SICI code
0040-4039(1994)35:48<8969:ANSAES>2.0.ZU;2-D
Abstract
The first stereo- and enantioselective syntheses of trans-9-alkyl-2-be nzyl-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 l kyl-1-methyl-1,2-dihydronaphthalenecarboxaldehyde (10). Homologation o f 10 followed by reductive amination using benzylamine gave 1-benzylam inoethyl-1-methyl-1,2-dihydronaphthalene (11). Mercuric acetate-assist ed cyclization of 11 followed by LAK reduction afforded (1S,5S,9R)-12.