Chiral Aluminum Catalyst System for the Enantioselective Addition of Vinylaluminum Reagents to Aldehydes: Metal Controlled Reversal of Enantioselectivity
Authors:
- 25 November 2016
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 358 (23) , 3688-3693
Abstract
A chiral aluminum catalyst system has been developed for the enantioselective vinylation of aldehydes. β,β‐Disubstituted (E)‐vinylaluminum reagents, generated regio‐ and stereoselectively by the carboalumination of terminal alkynes with trimethylalumunim (Me3Al), were used straightforwardly without transmetalation to vinyltitanium reagents in the subsequent enantioselective addition to aldehydes with a DPP‐H8‐BINOL‐derived chiral aluminum catalyst at low catalyst loading (5 mol%). The reaction afforded the corresponding enantiomerically enriched secondary allylic alcohols with a reversal of the selectivity observed in closely related reactions catalyzed by a chiral titanium complex derived from the same ligand. magnified imageKeywords
Funding Information
- KAKENHI from Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan (No. 15K05500)
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