A Hetero Diels–Alder Concerted vs. Aldol Stepwise Mechanism in the Cyclization of Silyloxyazadienes with Aldehydes: A Theoretical Study | Zendy

Bongini Alessandro | Zendy; Panunzio Mauro | Zendy

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A Hetero Diels–Alder Concerted vs. Aldol Stepwise Mechanism in the Cyclization of Silyloxyazadienes with Aldehydes: A Theoretical Study

Author(s) -

Bongini Alessandro,

Panunzio Mauro

Publication year - 2006

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200500611

Subject(s) - chemistry , aldehyde , concerted reaction , lewis acids and bases , aldol reaction , diels–alder reaction , formaldehyde , reaction mechanism , lewis acid catalysis , acid catalysis , stepwise reaction , mechanism (biology) , computational chemistry , organic chemistry , medicinal chemistry , stereochemistry , catalysis , kinetics , reaction rate constant , philosophy , epistemology , physics , quantum mechanics , order of reaction

The Diels–Alder reaction of 3‐silyloxy‐2‐azadiene with formaldehyde has been studied at the B3LYP/6‐31G* level of theory and the role played by a Lewis acid evaluated. It is shown that the reaction is preferred when the Lewis acid coordinates to the aldehyde oxygen. This coordination allows for a concerted as well as a stepwise mechanism for the cyclization. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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