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