ISSN:
0947-3440
Keywords:
(2R,3R)-1,4-Dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol
;
Boronic acids
;
Boronic esters
;
Cyclopropanation
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of enantiomerically pure cyclopropyl boronic esters 12a-d and 13a-d has been achieved. The high-yielding process involves the condensation of readily available alkenyl boronic acids 1a-d with (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol (10), Pd(II) acetate catalyzed cyclopropanation with diazomethane, and chromatographic separation of the diastereoisomers. The absolute configuration has been determined by converting 12a-d and 13a-d to the corresponding cyclopropanols (1R,2R)-4a+b/(1R,2S)-4c+d and (1S,2S)-4a+b/(1S,2R)-4c+d, respectively, compounds that allowed correlations to be made with previously published data.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719971118
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