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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.