Allene synthesis by an asymmetric Baylis-Hillman style reaction on vinylphosphine oxides

Citation
Dj. Fox et al., Allene synthesis by an asymmetric Baylis-Hillman style reaction on vinylphosphine oxides, J CHEM S P1, (18), 2001, pp. 2240-2249
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
18
Year of publication
2001
Pages
2240 - 2249
Database
ISI
SICI code
1472-7781(20010921):18<2240:ASBAAB>2.0.ZU;2-K
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- alpha -methylbenzylbenzylamine 2 in the presence of an aldehyde gave hydrox yphosphine oxides in good to moderate yields and moderate to poor enantiose lectivities. The hydroxyphosphine oxides undergo the Horner-Wittig eliminat ion reaction to produce allenes. Baylis-Hillman reactions of vinylic phosph ine oxides with tertiary amines were also investigated.