Diastereoselective reaction of 1-(arylsulfinyl)-2-naphthaldehydes

Authors
Nakamura, S Yasuda, H Watanabe, Y Toru, T
Citation
S. Nakamura et al., Diastereoselective reaction of 1-(arylsulfinyl)-2-naphthaldehydes, TETRAHEDR L, 41(21), 2000, pp. 4157-4160
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
21
Year of publication
2000
Pages
4157 - 4160
Database
ISI
SICI code
0040-4039(20000529)41:21<4157:DRO1>2.0.ZU;2-V
Abstract
Reactions of various 1-sulfinyl-2-naphthaldehydes with Grignard reagents we re examined. The naphthaldehyde having the 2,4,6-triisopropylphenylsulfinyl group gave the product with high stereoselectivity, possibly derived from the predominant rotamer around the C-S axis. The reaction of the chiral sul finylnaphthaldehyde with PhMgBr and subsequent elimination of the sulfinyl group gave the enantiomerically pure 2-naphthyl carbinol. (C) 2000 Elsevier Science Ltd. All rights reserved.