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3‐Bromopropenyl Methylcarbonate in Organic Synthesis: A Straightforward Approach to 4,5‐Disubstituted 5‐Vinyl‐1,3‐dioxolan‐2‐ones
Author(s) -
Lombardo Marco,
Pasi Filippo,
Trombini Claudio
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.200600290
Subject(s) - chemistry , conjugated system , dimethylformamide , indium , organic chemistry , reaction conditions , aldehyde , medicinal chemistry , grignard reaction , catalysis , polymer , solvent , reagent
The reaction of 3‐bromopropenyl methylcarbonate ( 2 ) with aliphatic or aromatic aldehydes, in the presence of indium metal in N , N ‐dimethylformamide, affords cis and trans 4,5‐disubstituted 5‐vinyl‐1,3‐dioxolan‐2‐ones 4 in very high isolated yields. Reactions may be run by adopting either one‐pot Barbier conditions or a two‐step Grignard protocol. The cis ‐ 4 / trans ‐ 4 ratio is controlled by the nature of the carbonyl compound: saturated aldehydes mainly afford cis ‐ 4 , whereas conjugated aldehydes favor the formation of trans ‐ 4 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)