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A highly efficient and stereospecific borane reduction of spiro[4,4]nonane-1,6-dione catalyzed by a chiral oxazaborolidine

✍ Scribed by Ching-Wen Lin; Chi-Ching Lin; Yue-Ming Li; Albert S.C Chan

Book ID: 104210357
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 147 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00606-7

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✦ Synopsis

A highly stereoselective and enantioselective reduction of racemic spiro[4.4]nonane-1,6-dione catalyzed by an oxazaborolidine reagent is described. The asymmetric reduction of the racemic spirodiketones resulted in enantiomerically pure spirodiols which are useful chiral auxiliaries and also key intermediates for the synthesis of other highly eective chiral ligands. The trans,trans-and cis,trans-spirodiols were prepared in high enantiopurity by employing chiral oxazaborolidine as the catalyst.

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