Enantioselective addition of diethylzinc to aldehydes catalyzed by 5-cis-substituted proline derivatives. Issue 1 (3rd January 2019)

• Record Type: Journal Article
• Authors: Prause, Felix; Wagner, Stefan; Breuning, Matthias
• Is Part Of: Tetrahedron. Volume 75:Issue 1(2019)
• Page Start: 94
• Page End: 101
• Publication Date: 2019-01-03
• Subjects: Enantioselective catalysis -- Chiral ligands -- Pyrrolidine -- Diethylzinc -- Asymmetric addition; OSNNAZNOFCLZHD-PKTZIBPZSA-N -- QNJPWFJAQRSJGS-NWDGAFQWSA-N -- RTQXVTGAAXMTBZ-NWDGAFQWSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.11.030
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 5- Cis -substituted prolinols, prolinamines, and prolinamine sulfonamides proved to be efficient ligands for the enantioselective addition of diethylzinc to aldehydes, providing up to 99% ee. The sense of asymmetric induction can be controlled by the nature of the exocyclic functional group (CPh2 OH vs. CH2 NHR vs. CH2 NHSO3 R). The additional 5- cis substituent exerts a strong beneficial effect on the chirality transfer since it rigidifies the catalyst structure. The stereochemical outcome of the reactions is discussed in detail on the respective transition states. Graphical abstract: