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N-Heterocyclic Carbene-Cu-Catalyzed Enantioselective Allenyl Conjugate Addition

Qinglei Chong, Shuoqing Zhang, Fengchang Cheng, Jiping Wang, Xin Hong, Fanke Meng

Org Lett. 2018 Nov 2;20(21):6896-6900.

PMID: 30350670

Abstract:

A catalytic enantioselective conjugate addition with commercially available allenylboronic acid pinacol ester as nucleophile promoted by a chiral copper complex of N-heterocyclic carbene (NHC) is disclosed. This process constitutes an unprecedented instance of the conjugate addition that introduces an allenyl group into α,β-unsaturated carbonyl compounds, affording products that are otherwise difficult to access in up to 92% yield, >98% allenyl addition selectivity and 96:4 enantiomeric ratio. DFT calculations were performed to elucidate the origins of enantioselectivity.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP865350170 Allenylboronic acid pinacol ester Allenylboronic acid pinacol ester 865350-17-0 Price
LS793369 N-[2-hydroxyethyl]benzamide-3-boronic acid, pinacol ester N-[2-hydroxyethyl]benzamide-3-boronic acid, pinacol ester Price
LS793445 4-(3-Ethylureido)-3-methoxyphenylboronic acid, pinacol ester 4-(3-Ethylureido)-3-methoxyphenylboronic acid, pinacol ester Price
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