ISSN:
1434-193X
Keywords:
Allylation
;
Allylsilanes
;
Amino alcohols
;
Domino reactions
;
Homoallylic alcohols
;
Homoallylic ketones
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The facial selective allylation of alkyl methyl ketones 1a-f in the presence of chiral 2-amino alcohol derivatives 2a-p by reaction with allylsilane 3 and a catalytic amount of TfOH to give the tertiary homoallylic ethers 8a-o and 9a-e is described. The best results were obtained with the 2-amino alcohol derivative 2p which affords a stereoselectivity of 18:1 even for the allylation of ethyl methyl ketone. The ethers 8 and 9, which contain a phenyl group at C-1 of the amino alcohol moiety, can be cleaved to give the corresponding homoallylic alcohols 5 by reduction with sodium or lithium in liquid ammonia.
Type of Medium:
Electronic Resource
Permalink
