Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 19, Pages 3760-3767Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800785
Keywords
Heck reaction; diastereoselectivity; enantioselectivity; noncovalent interactions; density functional calculations
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Funding
- National Science Foundation [CHE-1401700]
- FAPESP [2013/25849-9, 2017/01779-2, 2014/25770-6]
- University of Louisville
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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.
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