Diastereoselective [3+2]-photocycloaddition of chiral 1,4-naphthalenedicarboxylic esters to alkenes

Authors
Kubo, Y Yoshioka, M Nakajima, S Inamura, I
Citation
Y. Kubo et al., Diastereoselective [3+2]-photocycloaddition of chiral 1,4-naphthalenedicarboxylic esters to alkenes, TETRAHEDR L, 40(12), 1999, pp. 2335-2338
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
12
Year of publication
1999
Pages
2335 - 2338
Database
ISI
SICI code
0040-4039(19990319)40:12<2335:D[OC1>2.0.ZU;2-C
Abstract
[3+2]-Photocycloaddition of di-(-)-menthyl, di-(-)-8-phenylmenthyl, and di- (-)-bornyl 1,4-naphthalenedicarboxylates to alkenes, such as isobutene, sty rene, and alpha-methylstyrene, proceeded with diastereoselectivity, up to 6 2% diastereomeric excess (de), largely depending on the concavity of the au xiliary, steric bulk of the substituents of the alkenes, and reaction tempe rature. The de values remarkably increased with decrease of the reaction te mperature, and linear dependence of In(diastereomeric ratio) on 1/T was obs erved. (C) 1999 Elsevier Science Ltd. All rights reserved.