Acidity-directed synthesis of substituted gamma-butyrolactones from aliphatic aldehydes |
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| Authors: | Ramachandran P Veeraraghavan Pratihar Debarshi |
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| Institution: | Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu |
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| Abstract: | The strength of the Lewis or Br?nsted acids controls the formation of either beta,gamma-disubstituted-alpha-methylene-gamma-butyrolactones or gamma-substituted-alpha-alkylidene-gamma-butyrolactones via the lactonization or oxonia cope rearrangement-lactonization, respectively, of the borate intermediates resulting from the crotylboration of aliphatic aldehydes with ester-containing crotylboronates, such as (E)-methyl 2-boramethyl-2-butenoates. |
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