期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 25, 页码 7299-7302出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501832
关键词
allylic alcohols; asymmetric dienylation; boron; enantioselectivity; organocatalysis
资金
- National Natural Science Foundation of China [21303128, 21422305]
- Research Fund for the Doctoral Program of Higher Education of China [20130143120003]
- Fundamental Research Funds for the Central Universities [WUT: 2014-Ia-002]
Asymmetric C(sp) C(sp(2)) bond formation to give enantiomerically enriched 1,3-butadienyl-2-carbinols occurred through a homoallenylboration reaction between a 2,3-dienylboronic ester and aldehydes under the catalysis of a chiral phosphoric acid (CPA). A diverse range of enantiomerically enriched butadiene-substituted secondary alcohols with aryl, heterocyclic, and aliphatic substituents were synthesized in very high yield with high enantioselectivity. Preliminary density functional theory (DFT) calculations suggest that the reaction proceeds via a cyclic six-membered chairlike transition state with essential hydrogen-bond activation in the allene reagent. The catalytic reaction was amenable to the gram-scale synthesis of a chiral alkyl butadienyl adduct, which was converted into an interesting optically pure compound bearing a benzo-fused spirocyclic cyclopentenone framework.
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