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Synthesis of Enantiomerically Pure Cyclopropyl Boronic Esters

✍ Scribed by Luithle, Joachim E. A. ;Pietruszka, Jörg

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
737 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

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 la-d with (2R,3R)-1,4-dimethoxy-(1R,2S)-4c+d and (lS,2S)-4a+bl(lS,2R)-4c+d, respectively, 1,1,4,4-tetraphenyl-2,3-butanediol (lo), Pd(I1) acetate catalyzed cyclopropanation with diazomethane, and chromato-viously published data. graphic 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/ compounds that allowed correlations to be made with pre-

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Highly stable, enantiomerically pure cyclopropylboronic esters are desirable building blocks for the preparation of a plethora of different cyclopropane derivatives. Whereas trans-configured compounds proved to be readily available, we herein report the first synthesis of the corresponding cis-