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 | Zendy

Xie Peizhong | Zendy; Yang Jie | Zendy; Zheng Jie | Zendy; Huang You | Zendy

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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.

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