Sulfinylimidates as Chiral Amide Equivalents for Irreversible, Asymmetric Aldol Reactions.
A highly selective N-sulfinylimidate aldolization has been developed under mildly basic conditions leading to diastereopure products of high synthetic potential [e.g., E-sulfinylimidate I + PhCHO in presence of TiCl2(OiPr)2 and Et3N afforded aldol II with 97:3 dr (relative to the beta-diastereomeric alc.)]. The innate reversibility of this aldolization was suppressed by the use of titanium as the Lewis acid. An application of this methodol. via the synthesis of a potential neurotransmitter reuptake inhibitor is illustrated.
Références
- Titre
- Sulfinylimidates as Chiral Amide Equivalents for Irreversible, Asymmetric Aldol Reactions.
- Type de publication
- Article de revue
- Année de publication
- 2014
- Auteurs
- Bartrum, Hannah E., Viceriat Audrey, Carret Sébastien, and Poisson Jean-François
- Revue
- Org. Lett.
- Volume
- 16
- Pagination
- 1972–1975
- ISSN
- 1523-7052
Soumis le 12 avril 2018