Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of a-Halo Thioesters and Enolizable Aldehydes.
- Resource Type
- Article
- Authors
- Sauer, Scott J.; Garnsey, Michelle R.; Coltart, Don M.
- Source
- Journal of the American Chemical Society. 10/13/2010, Vol. 132 Issue 40, p13997-13999. 3p.
- Subject
- *ORGANIC synthesis
*CARBONYL compounds
*CHEMICAL reduction
*CARBON
ALDEHYDE reactivity
- Language
- ISSN
- 0002-7863
The direct addition of enolizable aldehydes and ct-halo thioesters to produce β-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic α-hydroxy aldehyde derivative is used. [ABSTRACT FROM AUTHOR]