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Highly Selective Allylation of Alkyl Methyl Ketones in the Presence of Chiral 2‐Amino Alcohol Derivatives
Author(s) -
Tietze Lutz F.,
Wegner Christoph,
Wulff Christian
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199808)1998:8<1639::aid-ejoc1639>3.0.co;2-w
Subject(s) - chemistry , alcohol , ketone , moiety , alkyl , stereoselectivity , organic chemistry , catalysis , medicinal chemistry , primary alcohol , lithium (medication) , medicine , endocrinology
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.