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Sequential Catalyst Phosphine/Secondary Amine Promoted [1+4]/Rearrangement Domino Reaction for the Construction of (2 H )‐Pyrans and 2‐Oxabicyclo[2.2.2]oct‐5‐ene Skeletons
Author(s) -
Xie Peizhong,
Yang Jie,
Zheng Jie,
Huang You
Publication year - 2014
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.201301872
Subject(s) - chemistry , synthon , catalysis , ene reaction , domino , amine gas treating , cascade reaction , carbonate , phosphine , pyran , organic chemistry , medicinal chemistry
Sequential catalysis of a [2+4] reaction between a Baylis–Hillman carbonate and a β,γ‐unsaturated α‐oxo ester for the synthesis of 2‐methyl‐2 H ‐pyran was developed. The use of a Morita–Baylis–Hillman carbonate as a C 2 synthon is first disclosed in this reaction. This method offers a new approach to the construction of 2‐methyl‐2 H ‐pyrans and 2‐oxabicyclo[2.2.2]oct‐5‐ene skeletons.