MECHANISTIC IMPLICATIONS OF STEREOSPECIFIC 1,5-HYDROGEN-ATOM TRANSFERIN THE FORMATION OF AN UNUSUAL ALLENE ENOATE PHOTOPRODUCT/

Authors
HASTINGS CA RINGGENBERG JD CARREIRA EM
Citation
Ca. Hastings et al., MECHANISTIC IMPLICATIONS OF STEREOSPECIFIC 1,5-HYDROGEN-ATOM TRANSFERIN THE FORMATION OF AN UNUSUAL ALLENE ENOATE PHOTOPRODUCT/, Tetrahedron letters, 38(51), 1997, pp. 8789-8792
Citations number
17
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
51
Year of publication
1997
Pages
8789 - 8792
Database
ISI
SICI code
0040-4039(1997)38:51<8789:MIOS1T>2.0.ZU;2-H
Abstract
Irradiation of allene-enoate 1 affords alkyne 3 as the major photoprod uct. Selectively deuterated analog d-1 affords a single diastereomer o n irradiation. This result supports a stepwise mechanism for enantiose lective [2+2]-photocycloadditions involving a 1,4-biradical intermedia te 2 which collapses to products more rapidly than it undergoes revers ion to starting material, resulting in the observed high levels of asy mmetric induction. (C) 1997 Elsevier Science Ltd.