Advanced search
Start date
Betweenand
Related content
(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Non-Covalent Substrate Directed Enantioselective Heck Desymmetrization of cis-Cyclohex-4-ene-1,2-diol: Synthesis of all cis Chiral 5-Aryl-cyclohex-3-ene-1,2-diols and Mechanistic Investigation

Full text
Author(s):
Angnes, Ricardo A. [1, 2] ; Thompson, Lee M. [1] ; Mashuta, Mark S. [1] ; Correia, Carlos R. D. [2] ; Hammond, Gerald B. [1]
Total Authors: 5
Affiliation:
[1] Univ Louisville, Chem Dept, Louisville, KY 40292 - USA
[2] Univ Estadual Campinas, Chem Dept, CP 6154, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: ADVANCED SYNTHESIS & CATALYSIS; v. 360, n. 19, p. 3760-3767, OCT 4 2018.
Web of Science Citations: 5
Abstract

Enantioselective substrate directed Heck reactions are desirable for the stereoselective synthesis of complex molecules. However, due to the coordination requirements of both chiral ligands and directing groups, such methodologies are underdeveloped. We report herein the desymmetrization of meso (1R,2S)-cyclohex-4-ene-1,2-diol in an enantioselective and substrate directed fashion. The method provides all cis substituted highly functionalized chiral allylic alcohols in a complementary fashion to other Heck protocols.The products were obtained in high enantioselectivities (higher than 95% ee) and moderate to high yields (38-87%). The noncovalent interactions responsible for the directing effect were elucidated through computational examination of relevant minima and transition structures. (AU)

FAPESP's process: 17/01779-2 - Powerful Partners: Ionic Promoters and the Enantioselective Heck-Matsuda Reaction
Grantee:Ricardo Almir Angnes
Support Opportunities: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 13/25849-9 - Application of the enantioselective Heck-Matsuda reaction for substrate oriented regioselective desymmetrizations
Grantee:Ricardo Almir Angnes
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Research Projects - Thematic Grants