Unusual reagent control of diastereoselectivity in the 1,2-addition of hard carbon nucleophiles to C-6-heteroatom substituted cyclohexenones

Authors
Lindsay, HA Salisbury, CL Cordes, W McIntosh, MC
Citation
Ha. Lindsay et al., Unusual reagent control of diastereoselectivity in the 1,2-addition of hard carbon nucleophiles to C-6-heteroatom substituted cyclohexenones, ORG LETT, 3(25), 2001, pp. 4007-4010
Citations number
66
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
25
Year of publication
2001
Pages
4007 - 4010
Database
ISI
SICI code
1523-7060(200112)3:25<4007:URCODI>2.0.ZU;2-I
Abstract
[GRAPHICS] A surprising and synthetically useful counterion-dependent reversal of dias tereoselectivity was found in 1,2-additions of hard carbon nucleophiles to C-6-heterosubstituted cyclohexenones. In general, Grignard reagents added s yn to the C-6-substituent and Li reagents added anti, although some excepti ons were found. Selectivities could be increased in some cases by appropria te choice of solvent and/or cosolvent.