37616-27-6Relevant academic research and scientific papers
Lewis acid catalysed M-ene, H-ene, and cycloaddition reactions of allylic stannanes and silanes with methyl propiolate
Dang, Hai-Shan,Davies, Alwyn G.
, p. 67 - 72 (2007/10/03)
The products of the reaction of methyl propiolate with cyclohexene and some allyl and cyclohex-2-enyl silanes and stannanes (H-ene and M-ene adducts, and [2+2] and [3+2] cycloadducts) have been determined, and rationlised in terms of the probable reaction mechanism. The allylstannanes show only the M-ene reactions to give a mixture of the E- and Z-adducts, and it has been confirmed that the reaction of allylsilanes can give both the [2+2] (cyclobutene) and [3+2] (cyclopentene) cycloadducts, which has been a matter of some dispute.
PALLADIUM-CATALYZED CROSS COUPLING OF ALLYL HALIDES WITH ORGANOTIN REAGENTS: A METHOD OF JOINING HIGHLY FUNCTIONALIZED PARTNERS REGIOSELECTIVELY AND STEREOSPECIFICALLY.
Sheffy,Godschalx,Stille
, p. 4833 - 4840 (2007/10/11)
The palladium-catalyzed reaction of allyl halides with aryl- and vinyltin reagents gives high yields of cross-coupled products. In the presence of 1-3 atm of carbon monoxide, ketones are obtained, resulting from cross coupling accompanied by carbon monoxide insertion. The reaction is mild and tolerant of a wide variety of functionalities (OH, OR, CN, CO//2R, CHO) on either the allyl chloride or the tin reagent. Coupling at the allyl halide partner proceeds with inversion of configuration at the carbon bearing the halide, with retention of geometry at the allylic double bond, and with a regioselectivity for the least-substituted carbon in the allylic framework. Retention of double-bond geometry is observed in the vinyltin partner.
