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Base‐Catalyzed Direct Aldolization of α‐Alkyl‐α‐Hydroxy Trialkyl Phosphonoacetates
Author(s) -
Corbett Michael T.,
Uraguchi Daisuke,
Ooi Takashi,
Johnson Jeffrey S.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201200559
Subject(s) - phosphonate , catalysis , alkyl , aldol reaction , chemistry , base (topology) , organic chemistry , combinatorial chemistry , medicinal chemistry , mathematics , mathematical analysis
Pass the P : Catalytic direct aldol addition of α‐hydroxy trialkyl phosphonacetates to aldehydes affords α‐hydroxy‐β‐phosphonyloxy ester products (see scheme). The fully substituted glycolate enolate intermediate is generated in situ under mild conditions by a [1,2] phosphonate–phosphate rearrangement. High enantioselectivity and dramatic enhancement of reaction diastereocontrol is realized by the application of chiral iminophosphorane catalysts.