Highly Diastereoselective Silyl‐Modified Sakurai Multicomponent Reaction | Zendy

Pospíšil Jiøí | Zendy; Kumamoto Takuya | Zendy; Markó István E. | Zendy

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Highly Diastereoselective Silyl‐Modified Sakurai Multicomponent Reaction

Author(s) -

Pospíšil Jiøí,

Kumamoto Takuya,

Markó István E.

Publication year - 2006

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.200600169

Subject(s) - dihydropyran , aldehyde , silylation , trimethylsilyl , silane , chemistry , condensation , condensation reaction , alcohol , organic chemistry , catalysis , physics , thermodynamics

The more the merrier : A multicomponent Sakurai reaction has been developed in which an efficient, highly diastereoselective three‐component condensation of an aldehyde 1 , allyl silane 2 , and silylated alcohol 3 is mediated by trimethylsilyl triflate (TMSOTf). Products such as 4 can serve as direct precursors to dihydropyran skeletons, which is demonstrated by the synthesis of a portion of (+)‐ambruticin. TBS= tert ‐butyldimethylsilyl.

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