Stereospecificity in the Lewis acid promoted allylation reaction of 3,3-disubstituted allyltins toward aldehydes

Authors
Nishigaichi, Y Takuwa, A
Citation
Y. Nishigaichi et A. Takuwa, Stereospecificity in the Lewis acid promoted allylation reaction of 3,3-disubstituted allyltins toward aldehydes, TETRAHEDR L, 40(1), 1999, pp. 109-112
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
1
Year of publication
1999
Pages
109 - 112
Database
ISI
SICI code
0040-4039(19990101)40:1<109:SITLAP>2.0.ZU;2-C
Abstract
The Lewis acid-promoted reaction of 3,3-disubstituted allyltins toward alde hydes was found to be stereospecific; the (E)-reagent gave syn-products and the (Z)-one gave anti-products. This is in contrast to that of 3-mono-subs tituted congeners which are known to react syn-stereoselectively regardless of their double bond geometry. The reaction was assumed to proceed via an acyclic syn-synclinal transition state. (C) 1998 Elsevier Science Ltd. All rights reserved.