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. 2014 Nov 26;136(47):16485-8.
doi: 10.1021/ja510113s. Epub 2014 Nov 12.

Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts

Hu Zhang  1 , Song Lin, Eric N Jacobsen
Affiliations

Enantioselective selenocyclization via dynamic kinetic resolution of seleniranium ions by hydrogen-bond donor catalysts

Hu Zhang et al. J Am Chem Soc. .

Abstract

Highly enantioselective selenocyclization reactions are promoted by the combination of a new chiral squaramide catalyst, a mineral acid, and an achiral Lewis base. Mechanistic studies reveal that the enantioselectivity originates from the dynamic kinetic resolution of seleniranium ions through anion-binding catalysis.

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Figures

Scheme 1
Scheme 1. Two Strategies for the Development of Enantioselective Selenofunctionalization Reactions
Scheme 2
Scheme 2. Derivatization of a Selenocyclization Product
Scheme 3
Scheme 3. DKR of Intermediate rac-Int-k with 5d
Scheme 4
Scheme 4. Proposed Catalytic Cycle
See this image and copyright information in PMC

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