Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 6, Pages 1394-1403Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704443
Keywords
asymmetric catalysis; cyclopropenes; hydroboration; protecting groups; rhodium
Categories
Funding
- Russian Foundation for Basic Research [15-03-02661]
- Ministry of Education and Science of the Russian Federation [02.a03.21.0008, 4.1196.2017]
- NIH Shared Instrumentation Grant [S10RR024664]
- NSF Major Research Instrumentation Grant [0329648]
Ask authors/readers for more resources
A full account on rhodium-catalyzed asymmetric, directed hydroboration of functionalized prochiral cyclopropenes affording enantiomerically enriched cyclopropylboronates is reported. The scope and limitations of two alternate directing groups, ester and carboxamide, are evaluated. It was found that hydroboration of esters appeared to be more sensitive to substitution in the aromatic ring of the substrates. Specifically, ortho-halogens were detrimental for diastereo- and enantioselectivity, possibly because of additional coordination with rhodium. In contrast, more Lewis-basic amide directing groups allowed for stronger chelation to the transition metal, leading to consistently high diastereo- and enantioselectivity in hydroboration across a broader range of substrates.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available