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Orthoester in Cyclodehydration of Carbamate-Protected Amino Alcohols under Acidic Conditions

Heemin Park, Yongseok Kwon, Jae Eui Shin, Woo-Jung Kim, Soonho Hwang, Seokwoo Lee, Sanghee Kim*

*College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea, Email: pennkimsnu.ac.kr

H. Park, Y. Kwon, J. E. Shin, W.-J. Kim, S. Hwang, S. Lee, S. Kim, Synthesis, 2017, 49, 2761-2767.

DOI: 10.1055/s-0036-1588750 (free Supporting Information)


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Abstract

An acid-promoted synthesis of azaheterocycles from N-carbamate-protected amino alcohols involves the activation of the hydroxyl group via the use of orthoesters. Despite the reduced nucleophilicity of carbamate nitrogen, this reaction system provides several types of pyrrolidines and piperidines in very good yields.

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Key Words

N-carbamates, cyclization, Lewis acids, azaheterocycles, pyrrolidines, orthoester, oxocarbenium


ID: J66-Y2017