Base‐Catalyzed Direct Aldolization of α‐Alkyl‐α‐Hydroxy Trialkyl Phosphonoacetates | Zendy

Corbett Michael T. | Zendy; Uraguchi Daisuke | Zendy; Ooi Takashi | Zendy; Johnson Jeffrey S. | Zendy

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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.

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