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
Revue
Org. Lett.
Volume
16
Pagination
1972–1975
ISSN
1523-7052
Soumis le 12 avril 2018