Synthesis of Chiral Spirocycles by the Enantioselective Domino Heck/Remote C(sp2)—H Alkylation Reaction Catalyzed by Palladium/Xu-Phos

doi:10.6023/cjoc202200026

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1569-1571.DOI: 10.6023/cjoc202200026 Previous Articles

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钯/Xu-Phos催化对映选择性多米诺Heck/远程C(sp²)—H烷基化反应合成手性螺环化合物

王曼曼^*()

河南师范大学化学化工学院河南新乡 453007

发布日期:2022-05-16
通讯作者: 王曼曼

Synthesis of Chiral Spirocycles by the Enantioselective Domino Heck/Remote C(sp²)—H Alkylation Reaction Catalyzed by Palladium/Xu-Phos

Manman Wang()

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Published:2022-05-16
Contact: Manman Wang

Cite this article

Manman Wang. Synthesis of Chiral Spirocycles by the Enantioselective Domino Heck/Remote C(sp²)—H Alkylation Reaction Catalyzed by Palladium/Xu-Phos[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1569-1571.

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Fig. & Tab. 3

Scheme 1. (a) Elegant examples of racemic spirocycles and (b) enantioselective cascade Heck/remote C(sp2)—H alkylation reaction

Scheme 2. Some representative 5,4-spirocycles Regents and conditions: ligand (22 mol%), Pd-P(tBu)3-G3 (10 mol%), Cs2CO3 (1.0 equiv.), KOAc (1.0 equiv.), H2O (10 equiv.), MTBE/iPr2O (1∶1, 4 mL), 110 oC

Scheme 3. (a) Synthesis of a pair of enantiomers and (b) substrates scope of 5,5-spirocycle derivatives Regents and conditions: Cs2CO3 (2.0 equiv.), Pd2(dba)3•CHCl3 (5 mol%), N-Me-Xu3 (20 mol%), MTBE (2 mL), 90 oC, 12~24 h.

References 8

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钯/Xu-Phos催化对映选择性多米诺Heck/远程C(sp²)—H烷基化反应合成手性螺环化合物

Synthesis of Chiral Spirocycles by the Enantioselective Domino Heck/Remote C(sp²)—H Alkylation Reaction Catalyzed by Palladium/Xu-Phos

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