Molybdenum-Catalyzed Synthesis of Stannylated Allylic Alcohol Derivatives and Their Synthetic Applications

Uli Kazmaier; Sandra Dörrenbächer; Alexander Wesquet; Simon Lucas; Manuela Kummeter

doi:10.1055/s-2006-958940

PSP

Molybdenum-Catalyzed Synthesis of Stannylated Allylic Alcohol Derivatives and Their Synthetic Applications

Uli Kazmaier*, Sandra Dörrenbächer, Alexander Wesquet, Simon Lucas, Manuela Kummeter
Institut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany
Fax: +49(681)3022409; e-Mail: u.kazmaier@mx.uni-saarland.de;

Abstract

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Abstract

Mo(CO)₃(CNt-Bu)₃ (MoBI₃) was found to be a suitable catalyst for the regioselective hydrostannation of several types of alkynes, especially propargyl alcohol derivatives, affording preferentially the α-stannylated products. If propargylic acetates are used, the stannylated allylic acetates produced are suitable substrates for Pd-catalyzed allylic alkylations. Allenyl carbinols also undergo regioselective hydrostannation in the presence of MoBI₃, because the allenyl carbinols are more reactive than alkynes, and therefore milder reaction conditions are possible. Allylstannanes are formed preferentially, which can easily be converted into allyl iodides or vinyl epoxides.

Key words

hydrostannation - allenes - allylic alcohols - molybdenum - stannanes

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References

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