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Title: Chelation and Stereodirecting Group Effects on Regio- and Diastereoselective Samarium(II)-Water Allylic Benzoate Reductions
SmI2(H2O)n reductions of allylic benzoates adjacent to a trisubstituted alkene occur in high yields with complete regioselectivity and good diastereoselectivity (up to 90:10) for substrates containing properly positioned stereodirecting- and chelating groups. The outcome of these reactions can be rationalized by ring conformation considerations of a proposed chelated organosamarium intermediate, and a mechanism involving intramolecular protonation by a samarium-bound water.  more » « less
Award ID(s):
1760918
PAR ID:
10167118
Author(s) / Creator(s):
; ;
Date Published:
Journal Name:
Synthesis
Volume:
52
Issue:
10
ISSN:
0039-7881
Page Range / eLocation ID:
1544 to 1560
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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