Allene synthesis by an asymmetric Baylis–Hillman style reaction on vinylphosphine oxides
- 15 August 2001
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 18,p. 2240-2249
- https://doi.org/10.1039/b104436m
Abstract
A novel reaction has been discovered with a mechanism similar to the Baylis–Hillman reaction. Reaction of a vinylic phosphine oxide with (R)-N-lithio-α-methylbenzylbenzylamine 2 in the presence of an aldehyde gave hydroxyphosphine oxides in good to moderate yields and moderate to poor enantioselectivities. The hydroxyphosphine oxides undergo the Horner–Wittig elimination reaction to produce allenes. Baylis–Hillman reactions of vinylic phosphine oxides with tertiary amines were also investigated.Keywords
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