使用双光氧化还原/钯催化对森田-贝利斯-希尔曼加合物进行对映选择性自由基S2型烷基化反应。
Enantioselective Radical S2-Type Alkylation of Morita-Baylis-Hillman Adducts Using Dual Photoredox/Palladium Catalysis.
作者信息
Bai Xiangbin, Qian Linlin, Zhang Hong-Hao, Yu Shouyun
机构信息
State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
出版信息
Org Lett. 2021 Nov 5;23(21):8322-8326. doi: 10.1021/acs.orglett.1c03064. Epub 2021 Oct 21.
An enantioselective radical alkylation of 4-alkyl-1,4-dihydropyridines with Morita-Baylis-Hillman (MBH) adducts has been reported. The S2-type products are predominant. This reaction is enabled by dual photoredox/palladium catalysis. The alkylation products are provided in good yields with good regio- and enantioselectivity. The use of Ding's spiroketal-based bis(phosphine) (SKP) ligand is crucial to achieving satisfactory regio- and enantioselectivity. The resultant α,β-unsaturated ester can be easily reduced to a synthetically useful chiral allyl alcohol.
已有报道4-烷基-1,4-二氢吡啶与森田-贝利斯-希尔曼（MBH）加合物的对映选择性自由基烷基化反应。S2型产物占主导。该反应由双光氧化还原/钯催化实现。烷基化产物以良好的产率、区域选择性和对映选择性得到。使用丁氏基于螺缩酮的双（膦）（SKP）配体对于实现令人满意的区域选择性和对映选择性至关重要。所得的α,β-不饱和酯可轻松还原为具有合成用途的手性烯丙醇。
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