Vinyl Dihydropyrans and Dihydrooxazines: Cyclizations of Catalytic Ruthenium Carbenes Derived from Alkynals and Alkynones | Zendy

Cambeiro Fermín | Zendy; López Susana | Zendy; Varela Jesús A. | Zendy; Saá Carlos | Zendy

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Vinyl Dihydropyrans and Dihydrooxazines: Cyclizations of Catalytic Ruthenium Carbenes Derived from Alkynals and Alkynones

Author(s) -

Cambeiro Fermín,

López Susana,

Varela Jesús A.,

Saá Carlos

Publication year - 2014

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.201400675

Subject(s) - diazomethane , nucleophile , morpholine , chemistry , ruthenium , catalysis , trimethylsilyl , carbene , oxazines , organic chemistry , combinatorial chemistry

A novel synthesis of 2‐vinyldihydropyrans and dihydro‐1,4‐oxazines (morpholine derivatives) from alkynals and alkynones has been developed. The cyclizations require a mild generation of catalytic ruthenium carbenes from terminal alkynes and (trimethylsilyl)diazomethane followed by trapping with carbonyl nucleophiles. Mechanistic aspects of the new cyclizations are discussed.

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