S(N)2 ring opening of beta-lactones: An alternative to catalytic asymmetric conjugate additions

Merging catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions with ensuing Grignard-mediated ring opening of the derived enantiomerically enriched beta-lactones is presented as a generally useful asymmetric synthesis of beta-disubstituted carboxylic acids. Enantiomerically enri...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 67; no. 14; pp. 4680 - 4683
Main Authors Nelson, SG, Wan, ZH, Stan, MA
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 12.07.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENTS
PROPIOLACTONES
ALPHA-AMINO-ACIDS
PHOSPHORAMIDITE
STEREOSELECTIVE-SYNTHESIS
1,4-ADDITION
LIGAND
MICHAEL ADDITIONS
EFFICIENT
DERIVATIVES
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ISSN0022-3263
1520-6904
DOI10.1021/jo025519n

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Summary:Merging catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions with ensuing Grignard-mediated ring opening of the derived enantiomerically enriched beta-lactones is presented as a generally useful asymmetric synthesis of beta-disubstituted carboxylic acids. Enantiomerically enriched beta-lactones are subject to efficient S(N)2 ring opening with a variety of copper-modified alkyl Grignard reagents, including highly branched nucleophiles. Considerable structural variation in the lactone electrophile is also tolerated. Phenyl- and vinyl-derived organometallics are not efficient nucleophiles for the ring-opening reactions.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo025519n