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

Angewandte Chemie (International ed. in English) (2016-06-09)
Daniel W Robbins, KyungA Lee, Daniel L Silverio, Alexey Volkov, Sebastian Torker, Amir H Hoveyda
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(S)-2-((2-Hydroxy-3-(triphenylsilyl)benzyl)amino)-N,N,3-trimethylbutanamide, ≥95%
Sigma-Aldrich
(S)-2-((3-(tert-butyl)-2-hydroxybenzyl)amino)-N,N,3-trimethylbutanamide, ≥95%
Sigma-Aldrich
(S)-2-((2-Hydroxy-3-methylbenzyl)amino)-N,N,3-trimethylbutanamide, ≥95%

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