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ChemInform Abstract: A Highly Enantioselective and Diastereoselective Synthesis of Cyclobutanes via Boronic Esters.

โœ Scribed by Hon-Wah Man; William C. Hiscox; Donald S. Matteson

Publisher
John Wiley and Sons
Year
2010
Weight
30 KB
Volume
30
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

A Highly Enantioselective and Diastereoselective Synthesis of Cyclobutanes via Boronic Esters. -Deprotection of enantiopure boronate (II) with LDA provides a spirocyclic boronate which rearranges in high enantiopurity to the cyclobutanone (IV) on treatment with catalytic MgBr 2 . Interestingly, no cyclobutane formation is obtained in the absence of magnesium halide. Products of type (IV) are potential synthons for a broad spectrum of substances [cf. monoterpenoid skeleton (VI)].

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