Stereoselective Synthesis of Fused Spiroindolines via Tandem Mannich/Intramolecular Aminal Formation

Xie, Xingang; Wang, Zhengshen; Mei, Ruoming; Zheng, Huaiji; Wang, Xiaolei; Zhang, Ling; Qi, Jing; She, Xuegong

doi:10.1021/jo302404v

Cited by 12 publications

(1 citation statement)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Bearing in mind that the formation of tetrahydro β-carbolines occurs through the Pictet–Spengler reaction, − we envisaged that the regeneration of the latent N -acyliminium ion (B′) in type A′ dipeptides could provide access to the corresponding aminoacetal derivatives (C′) via α-functionalization of the amine (Scheme ). − …”

Section: Introductionmentioning

confidence: 99%

Ring-Fused Cyclic Aminals from Tetrahydro-β-carboline-Based Dipeptide Compounds

et al. 2017

View full text Add to dashboard Cite

An acid- and oxidant-promoted intramolecular cyclization of a tetrahydro-β-carboline-based dipeptide has been developed to prepare new indole-fused aminoacetals. This approach involves N-acyliminium formation from readily available precursors and cyclization under mild reaction conditions. The diastereoselectivity in the formation of the products is influenced by the specific substituents of the starting reagents, which has been rationalized analyzing the energy profile of the related reactions and the relative stability of the proposed structures based on DFT computational methods.

show abstract

Section: Introductionmentioning

confidence: 99%

Ring-Fused Cyclic Aminals from Tetrahydro-β-carboline-Based Dipeptide Compounds

et al. 2017

View full text Add to dashboard Cite

show abstract

Practical Synthesis of Chromeno[2,3‐b]indole Skeleton via an Aldehyde Group Insertion/Aromatization Strategy

Liu

Yue

et al. 2017

Chemistry An Asian Journal

View full text Add to dashboard Cite

The synthesis of chromeno[2,3-b]indole from simple starting materials remains a demanding process. Herein, 2-bromoindole undergoes nucleophilic attack from salicylaldehyde, followed by intramolecular insertion of an aldehyde group and aromatization to generate the desired chromeno[2,3-b]indoles. Moreover, various functional groups were tolerated and a gram-scale synthesis of the product could be achieved under the optimized condition.

show abstract