Tandem Aldol−Allylation and Aldol−Aldol Reactions with Ketone-Derived Enolsilanes:  Highly Diastereoselective Single-Step Synthesis of Complex Tertiary Carbinols

A new tandem aldol−allylation reaction employing ketone-derived enolates has been developed that leads to the rapid, diastereoselective synthesis of tertiary carbinol containing fragments with relevance to polyketide natural product synthesis. In addition, the use of ketone-derived enolates has led...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2005-09, Vol.127 (37), p.12806-12807
Main Authors: Wang, Xiaolun, Meng, Qinglin, Perl, Nicholas R, Xu, Yue, Leighton, James L
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Aliphatic compounds
Alkylation
Chemistry
Exact sciences and technology
Ketones - chemical synthesis
Ketones - chemistry
Methanol - analogs & derivatives
Methanol - chemical synthesis
Molecular Conformation
Organic chemistry
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
Preparations and properties
Stereoisomerism
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Summary:A new tandem aldol−allylation reaction employing ketone-derived enolates has been developed that leads to the rapid, diastereoselective synthesis of tertiary carbinol containing fragments with relevance to polyketide natural product synthesis. In addition, the use of ketone-derived enolates has led to the development of a new tandem aldol−aldol reaction.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja053593s