Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles

doi:10.6023/cjoc202302017

Abstract

A Pd-catalyzed decarboxylation strategy for the efficient synthesis of cyclohepta[b]indoles in good yields with good to excellent enantioselectivities and moderate diastereoselectivities is reported. In this procedure, viny indoloxazolidones were activated by Pd catalyst to generate zwitterionic intermediates in situ, which were then trapped by the electro-deficient diene species via the asymmetric [3＋4] cycloaddition process.

Key words: decarboxylation, cyclohepta[b]indoles, asymmetric, cycloadditions

Cite this article

Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877.

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Entry ^a	Ligand	Solvent	Yield^b/%	dr^c	ee^d/%
1	L1	DCM	83	10.2∶1	23
2	L2	DCM	73	7.6∶1	68
3	L3	DCM	93	10.1∶1	31
4	L4	DCM	44	2.9∶1	12
5	L5	DCM	59	4.0∶1	75
6	L6	DCM	76	3.5∶1	81
7	L7	DCM	45	3.4∶1	88
8	L8	DCM	70	4.0∶1	87
9	L9	DCM	73	3.3∶1	89
10	L10	DCM	74	5.2∶1	95
11	L11	DCM	43	>20∶1	68
12	L12	DCM	83	>20∶1	67
13	L10	THF	36	2.8∶1	86
14	L10	PhMe	30	1.1∶1	56
15	L10	CHCl₃	76	5.1∶1	94
16	L10	DCE	36	2.9∶1	44

Entry ^a	Ligand	Solvent	Yield^b/%	dr^c	ee^d/%
1	L1	DCM	83	10.2∶1	23
2	L2	DCM	73	7.6∶1	68
3	L3	DCM	93	10.1∶1	31
4	L4	DCM	44	2.9∶1	12
5	L5	DCM	59	4.0∶1	75
6	L6	DCM	76	3.5∶1	81
7	L7	DCM	45	3.4∶1	88
8	L8	DCM	70	4.0∶1	87
9	L9	DCM	73	3.3∶1	89
10	L10	DCM	74	5.2∶1	95
11	L11	DCM	43	>20∶1	68
12	L12	DCM	83	>20∶1	67
13	L10	THF	36	2.8∶1	86
14	L10	PhMe	30	1.1∶1	56
15	L10	CHCl₃	76	5.1∶1	94
16	L10	DCE	36	2.9∶1	44

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钯催化不对称[3＋4]环加成构建吲哚并环庚烷