Spiro[4,4]-1,6-nonadiene-based diphosphine oxides in lewis base catalyzed asymmetric double-aldol reactions
Panke Zhang1, Zhaobin Han, Zheng Wang
1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032 (P. R. China).
Abstract:
Symmetry swap: A C2 -chiral spiro diphosphine oxide (SpinPO) has been found to be highly efficient and enantioselective in the catalysis of double-aldol reactions of ketones and aldehydes to give the corresponding optically active double-aldol products, which can be readily transformed into optically active C3 - and pseudo-C3 -symmetric molecules.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

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