Enantioselective electrochemical oxidation of enol acetates using a chiral supporting electrolyte.

Abstract:

:Anodic oxidation of 1-acetoxy-3,4-dihydronaphthalene (1) and alpha-acetoxy-beta-alkylstyrenes (3) at -78 degrees C in a mixed solvent of acetonitrile (CH(3)CN), tetrahydrofuran (THF), and acetic acid (AcOH) containing (S)-tetraethylammonium camphorsulfonate as a chiral supporting electrolyte brought about enantioselective formation of the corresponding 2-acetoxy-1-tetralones (2) and (R)-2-acetoxy-1-phenyl-1-alkanone (4) with maximum enantiomeric excess (ee) of 44% and 21%, respectively. Introduction of a 7-methoxy group into 1 and increase in bulkiness of a beta-alkyl group in 3 resulted in improvement of enantioselectivity of the reactions.

journal_name

Chirality

journal_title

Chirality

authors

Maekawa H,Itoh K,Goda S,Nishiguchi I

doi

10.1002/chir.10165

subject

Has Abstract

pub_date

2003-01-01 00:00:00

pages

95-100

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

15

pub_type

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