3 years ago

Highly Enantioselective Allylation of Ketones: An Efficient Approach to All Stereoisomers of Tertiary Homoallylic Alcohols

Highly Enantioselective Allylation of Ketones: An Efficient Approach to All Stereoisomers of Tertiary Homoallylic Alcohols
Marian Guder, Julie Schmauck, Marcus Brauns, Marvin Mantel, Jörg Pietruszka, Martin Breugst
An optimized protecting group for allylboronates allowed the use of ketones in order to synthesize all isomers of quaternary homoallylic alcohols with high enantioselectivities. All symmetric isomers of the allylboronate were prepared in high yields and diastereoselectivities using Sn2′ reactions. The improved reactivity of the novel protecting group was verified by following the reaction kinetics with 1H NMR spectroscopy. Mechanistic studies using DFT calculations were conducted to investigate the new findings. Thus, the stereochemical outcome and enhanced reactivity can be rationalized. Any way you want it: Rational design of novel allylboronates with increased reactivity for the highly selective synthesis of all stereoisomers of tertiary homoallylic alcohols. The conveniently stable compounds allow easy access of multiple examples under ambient conditions. Comprehensive insight on mechanistic details is provided by DFT calculations.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701740

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