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

doi:10.1055/s-0036-1588750

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

Seoul National University

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

The first acid-promoted reaction system to form azaheterocycles from N -carbamate-protected amino alcohols is described. The reaction 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 good to high yields. Using this protocol, prolinol derivatives can also be synthesized from carbamate-protected amino diols with regio- and stereoselectivity.

Original language	English
Pages (from-to)	2761-2767
Number of pages	7
Journal	Synthesis (Germany)
Volume	49
Issue number	12
DOIs	https://doi.org/10.1055/s-0036-1588750
State	Published - 19 Jun 2017
Externally published	Yes

Keywords

azaheterocycles
cyclization
Lewis acids
N -carbamate
orthoester
oxocarbenium

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10.1055/s-0036-1588750

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title = "Orthoester in Cyclodehydration of Carbamate-Protected Amino Alcohols under Acidic Conditions",

abstract = "The first acid-promoted reaction system to form azaheterocycles from N -carbamate-protected amino alcohols is described. The reaction 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 good to high yields. Using this protocol, prolinol derivatives can also be synthesized from carbamate-protected amino diols with regio- and stereoselectivity.",

keywords = "azaheterocycles, cyclization, Lewis acids, N -carbamate, orthoester, oxocarbenium",

author = "Heemin Park and Yongseok Kwon and Shin, \{Jae Eui\} and Kim, \{Woo Jung\} and Soonho Hwang and Seokwoo Lee and Sanghee Kim",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart.New York.",

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language = "English",

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T1 - Orthoester in Cyclodehydration of Carbamate-Protected Amino Alcohols under Acidic Conditions

AU - Park, Heemin

AU - Kwon, Yongseok

AU - Shin, Jae Eui

AU - Kim, Woo Jung

AU - Hwang, Soonho

AU - Lee, Seokwoo

AU - Kim, Sanghee

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart.New York.

PY - 2017/6/19

Y1 - 2017/6/19

N2 - The first acid-promoted reaction system to form azaheterocycles from N -carbamate-protected amino alcohols is described. The reaction 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 good to high yields. Using this protocol, prolinol derivatives can also be synthesized from carbamate-protected amino diols with regio- and stereoselectivity.

AB - The first acid-promoted reaction system to form azaheterocycles from N -carbamate-protected amino alcohols is described. The reaction 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 good to high yields. Using this protocol, prolinol derivatives can also be synthesized from carbamate-protected amino diols with regio- and stereoselectivity.

KW - azaheterocycles

KW - cyclization

KW - Lewis acids

KW - N -carbamate

KW - orthoester

KW - oxocarbenium

UR - https://www.scopus.com/pages/publications/85015258103

U2 - 10.1055/s-0036-1588750

DO - 10.1055/s-0036-1588750

M3 - Article

AN - SCOPUS:85015258103

SN - 0039-7881

VL - 49

SP - 2761

EP - 2767

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 12

ER -

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

Abstract

Keywords

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