Abstract
Complementary allylation conditions were developed for the synthesis of both diastereomers of tertiary homoallylic alcohols. Treatment of camphor N-tosylpyrazolidinone derived α-ketoamides with allyltributylstannane afforded both the individual homoallylic alcohols in high optical purity (up to 98% de) when the reaction was carried out in the presence of Sn(OTf)2 and PdCl2, respectively. The stereochemical outcome and reversal of stereoselectivity in the reaction are proposed based on 13C NMR and FTIR studies.
Original language | English |
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Pages (from-to) | 887-893 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 62 |
Issue number | 5 |
DOIs | |
Publication status | Published - 2006 Jan 30 |
Keywords
- Allylation
- Chiral auxiliary
- Reversal of stereoselectivity
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry