Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Aldehydes by Cooperative Catalysis of Palladium Complex and Chiral Squaramide

doi:10.6023/A18070291

Acta Chim. Sinica ›› 2018, Vol. 76 ›› Issue (11): 874-877.DOI: 10.6023/A18070291 Previous Articles Next Articles

Special Issue: 有机小分子-金属协同催化

Communication

钯配合物与手性方酰胺协同催化的乙烯基碳酸乙烯酯与醛的不对称脱羧环加成反应

Khan Ijaz^a, 李红芳^a,b, 吴学^b, 张勇健^a

a. 上海交通大学化学化工学院上海 200240;
b. 延边大学理学院化学系延吉 133002

投稿日期:2018-07-20 发布日期:2018-11-08
通讯作者: 张勇健 E-mail:yjian@sjtu.edu.cn
基金资助:
项目受国家自然科学基金（No.21572130）资助.

Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Aldehydes by Cooperative Catalysis of Palladium Complex and Chiral Squaramide

Khan Ijaz^a, Li Hongfang^a,b, Wu Xue^b, Zhang Yong Jian^a

a. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China;
b. Department of Chemistry, Yanbian University, Yanji, Jilin 133002, China

Received:2018-07-20 Published:2018-11-08
Contact: 10.6023/A18070291 E-mail:yjian@sjtu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572130).

1. Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Aldehydes by Cooperative Catalysis of Palladium Complex and Chiral Squaramide.PDF(2318KB)

Abstract

Chiral tertiary alcohols are ubiquitous in medicinally relevant agents and biologically active natural products. Although some catalytic asymmetric approaches for the synthesis of chiral tertiary alcohols have been reported, the development of efficient methods for enantioselective construction of tertiary alcohols is still highly appealing. Most recently, we have developed Pd-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates (VECs) with formaldehyde to construct tertiary alcohol derivatives. The reaction was catalyzed by the chiral palladium complex with a chiral phosphoramidite to afford methylene acetal protected tertiary vinylglycols in high efficiency. Since the pioneer works by Gong and Takemoto respectively for the allylic substitution under cooperative catalysis of palladium complex and chiral phase-transfer catalyst, the asymmetric allylic substitution synergistically catalyzed by transition metal and organocatalyst has recently attracted a great deal of attention. However, there have been no reports on the combination of transition-metal and squaramide for the allylic alkylation. In this communication, we will report the asymmetric decarboxylative cycloaddition of VECs with formaldehyde under cooperative catalytic system of achiral palladium complex and chiral squaramide. With combination of palladium complex in situ generated from Pd₂(dba)₃·CHCl₃ (2.5 mol%) and achiral phosphine ligand L4 (10 mol%) and chiral squaramide OC2 (25 mol%) as cooperative catalysts, the reaction of VECs with paraformaldehyde (10 equiv.) proceeded smoothly to give desired tertiary alcohol derivatives in good yields (51%~65%) with moderate enantioselectivities (62%~79% ee). The reaction conditions are also suitable for the reaction of VEC with electronic deficient arylaldehydes to afford desired products in high yields with good enantioselectivities, although the catalytic system is less effective for the control of the diastereoselectivities. Although the enantioselectivity of the reaction is not significantly high, we firstly demonstrated that the chiral induction for the cycloaddition reaction could be achieved under the cooperative catalytic system of achiral palladium complex and chiral squaramide. The detail reaction mechanism and stereochemical outcome are currently underway, and will be reported in due course.

Key words: cooperative catalysis, palladium-catalyzed reaction, chiral squaramide, asymmetric cycloaddition, chiral tertiary alcohol

Cite this article

Khan Ijaz, Li Hongfang, Wu Xue, Zhang Yong Jian. Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Aldehydes by Cooperative Catalysis of Palladium Complex and Chiral Squaramide[J]. Acta Chim. Sinica, 2018, 76(11): 874-877.

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钯配合物与手性方酰胺协同催化的乙烯基碳酸乙烯酯与醛的不对称脱羧环加成反应

Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Aldehydes by Cooperative Catalysis of Palladium Complex and Chiral Squaramide

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