NDLI: Practical and Broadly Applicable Catalytic Enantioselective Additions of Allyl-B(pin) Compounds to Ketones and α-Ketoesters

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Practical and Broadly Applicable Catalytic Enantioselective Additions of Allyl-B(pin) Compounds to Ketones and α-Ketoesters

Content Provider	Scilit
Author	Robbins, Daniel W. Lee, Kyunga Silverio, Daniel L. Volkov, Alexey Torker, Sebastian Hoveyda, Amir H.
Copyright Year	2016
Description	Journal: Angewandte Chemie International Edition A set of broadly applicable methods for efficient catalytic additions of easy-to-handle allyl-B(pin) (pin=pinacolato) compounds to ketones and acyclic α-ketoesters was developed. Accordingly, a large array of tertiary alcohols can be obtained in 60 to >98 % yield and up to 99:1 enantiomeric ratio. At the heart of this development is rational alteration of the structures of the small-molecule aminophenol-based catalysts. Notably, with ketones, increasing the size of a catalyst moiety (tBu to SiPh3 ) results in much higher enantioselectivity. With α-ketoesters, on the other hand, not only does the opposite hold true, since Me substitution leads to substantially higher enantioselectivity, but the sense of the selectivity is reversed as well.
Related Links	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4978177/pdf
Ending Page	9614
Page Count	5
Starting Page	9610
ISSN	14337851
e-ISSN	15213773
DOI	10.1002/anie.201603894
Journal	Angewandte Chemie International Edition
Issue Number	33
Volume Number	55
Language	English
Publisher	Wiley-Blackwell
Publisher Date	2016-06-07
Access Restriction	Open
Subject Keyword	Journal: Angewandte Chemie International Edition Organic Chemistry Enantioselective Synthesis Homoallylic Alcohols Homogeneous Catalysis
Content Type	Text
Resource Type	Article
Subject	Chemistry Catalysis

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