Organocatalytic Access to C1-Functionalized Indolizines via Remote Stereocontrolled Construction of Axially Chiral Allenes
Xuan Zhang , Xu-Hua Jiang , Chun-Dong Huang , Cheng Gao , Shao-Fei Ni , Qi-Jian Ni
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (21) : 2749 -2755.
Organocatalytic Access to C1-Functionalized Indolizines via Remote Stereocontrolled Construction of Axially Chiral Allenes
We present here a straightforward protocol for the enantioselective synthesis of axially chiral tetrasubstituted allenes enabled by chiral phosphoric acid (CPA)-catalyzed 1,8-addition of indolizines to propargylic alcohols. This strategy achieves enantioselective and regioselective C1-functionalization of indolizines under mild reaction conditions with low catalyst loading, broad functional group tolerance (35 examples), and excellent enantioselectivities (up to 96% ee). Moreover, the scale-up reaction and late-stage C3-functionalizations demonstrated its potential applications. DFT calculations were carried out to clarify the reaction mechanism and the origin of enantio- and regioselective control.
Asymmetric catalysis / Enantioselectivity / Organocatalysis / Chiral allenes / Indolizines / 1,8-Conjugate addition / Regioselectivity / Chiral phosphoric acid / Axial chirality
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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