Highly diastereoselective additions of methoxyallene and acetylenes to chiral alpha-keto amides

alpha -Keto amides bearing (S)-indoline chiral auxiliaries reacted with lithiated methoxyallene or lithium acetylides to produce the corresponding dihydrofuranones 7 through formation of the tertiary alpha -hydroxy allenes, or tertiary alpha -hydroxy acetylenes, respectively, at -78 degreesC with high diastereoselectivities (up to > 99% de).
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2001
Language
ENG
Keywords

TERTIARY HOMOALLYL ALCOHOLS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE ALKYNYLATION; LITHIATED METHOXYALLENE; LEWIS-ACIDS; ALDEHYDES; ESTERS; 3(2H)-DIHYDROFURANONES; ALKOXYALLENES

Citation

CHEMICAL COMMUNICATIONS, pp.996 - 997

ISSN
1359-7345
URI
http://hdl.handle.net/10203/3875
Appears in Collection
CH-Journal Papers(저널논문)
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