Regioselective Carbonylation of trans-Disubstituted Epoxides to β-Lactones: A Viable Entry into syn-Aldol-Type Products | Zendy

Michael Mulzer | Zendy; Bryan T. Whiting | Zendy; Geoffrey W. Coates | Zendy

Open Access

Regioselective Carbonylation of trans-Disubstituted Epoxides to β-Lactones: A Viable Entry into syn-Aldol-Type Products

Author(s) -

Michael Mulzer,

Bryan T. Whiting,

Geoffrey W. Coates

Publication year - 2013

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja405151n

Subject(s) - chemistry , aldol reaction , regioselectivity , carbonylation , catalysis , organic chemistry , epoxide , carbon monoxide

Two new catalysts are reported for the regioselective carbonylation of trans-disubstituted epoxides to cis-β-lactones. The two catalysts display high and opposing selectivities, which generally are difficult to achieve for this class of epoxides. The resulting β-lactones are well-defined precursors for a wide variety of aldol-type compounds. Altogether, carbonylation of disubstituted epoxides is established as a viable and economical entry into syn- and anti-aldol products.

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