1-phenyl-2-(1-pyrrolidinyl)-1-propanol as a chiral catalyst for the highly enantioselective addition of dialkylzincs to five-membered heterocyclic aldehydes

(1S,2R)- and (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol catalyze the enantioselective addition of dialkylzincs to furaldehydes, thiophenecarbaldehydes, and 1-(p-tosyl)-2-pyrrolecarbaldehyde to afford the corresponding enantiomerically enriched sec-alcohols with up to 87% enantiomeric excess.

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Bibliographic Details
Published inHeterocycles Vol. 51; no. 11; pp. 2753 - 2758
Main Authors Sato, Saito, T, Omiya, D, Takizawa, Y, Soai, K
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.11.1999
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REVERSE-TRANSCRIPTASE INHIBITOR
SHARPLESS REAGENT
ALCOHOLS
2-FURYLCARBINOLS
ASYMMETRIC-SYNTHESIS
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Summary:(1S,2R)- and (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol catalyze the enantioselective addition of dialkylzincs to furaldehydes, thiophenecarbaldehydes, and 1-(p-tosyl)-2-pyrrolecarbaldehyde to afford the corresponding enantiomerically enriched sec-alcohols with up to 87% enantiomeric excess.
ISSN:0385-5414
DOI:10.3987/com-99-8673