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

by Lindsay, Harriet A.; Salisbury, Catherine L.; Cordes, Wally; McIntosh, Matthias C.

[GRAPHICS] A surprising and synthetically useful counterion-dependent reversal of diastereoselectivity was found in 1,2-additions of hard carbon nucleophiles to C-6-heterosubstituted cyclohexenones. In general, Grignard reagents added syn to the C-6-substituent and Li reagents added anti, although some exceptions were found. Selectivities could be increased in some cases by appropriate choice of solvent and/or cosolvent.

Journal
Organic Letters
Volume
3
Issue
25
Year
2001
Start Page
4007-4010
URL
https://dx.doi.org/10.1021/ol016673j
ISBN/ISSN
1523-7052; 1523-7060
DOI
10.1021/ol016673j