Synthesis of trisubstituted alkenes by reductive dehydroxylation of Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3

Chandrasekhar, S. ; Chandrashekar, G. ; Vijeender, K. ; Srinivasa Reddy, M. (2006) Synthesis of trisubstituted alkenes by reductive dehydroxylation of Baylis-Hillman adducts using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3 Tetrahedron Letters, 47 (20). pp. 3475-3478. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2006.03.014

Abstract

B(C6F5)3 as a catalyst and polymethylhydrosiloxane as a hydride source have been employed for the reductive dehydroxylation of Baylis-Hillman adducts wherein the hydride adds in an SN2' manner onto the unactivated allyl alcohol moiety with concomitant elimination of the hydroxy group along with double bond migration. The products formed were found to be E in the case of ester adducts and Z in the case of nitrile adducts.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Baylis-Hillman Adducts; E and Z-trisubstituted Alkenes; PMHS-B(C6F5)3; Dehydroxylation
ID Code:62396
Deposited On:22 Sep 2011 03:29
Last Modified:22 Sep 2011 03:29

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