Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines

Authors
Bach, T Pelkmann, C Harms, K
Citation
T. Bach et al., Facial diastereoselectivity in the [2+2]-photocycloaddition of chiral vinylglycine-derived N,N-diallyl amines, TETRAHEDR L, 40(11), 1999, pp. 2103-2104
Citations number
4
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
11
Year of publication
1999
Pages
2103 - 2104
Database
ISI
SICI code
0040-4039(19990312)40:11<2103:FDIT[O>2.0.ZU;2-P
Abstract
The vinylglycine-derived N-cinnamyl-N-allyl carbamates 1, 4 and 7 were prep ared and their sensitized intramolecular [2+2]-photocycloaddition to the ex o-products 2, 5 and 6 was studied (53-77% yield). Perfect facial diastereos election (d.r. = >95/5) was observed in the photocycloaddition of the rigid oxazolidinone 4 and of the conformationally fixed acyclic carbamate 7. (C) 1999 Elsevier Science Ltd. All rights reserved.