Expedient synthesis of chiral homoallylamines via N, O-acetal TMS ethers and its application

Young Ger Suh; Jaebong Jang; Hwayoung Yun; Sae Mi Han; Dongyun Shin; Jae Kyung Jung; Jong Wha Jung

doi:10.1021/ol202573s

Expedient synthesis of chiral homoallylamines via N, O-acetal TMS ethers and its application

Young Ger Suh, Jaebong Jang, Hwayoung Yun, Sae Mi Han, Dongyun Shin, Jae Kyung Jung, Jong Wha Jung

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

9 Scopus citations

Abstract

A highly stereoselective and efficient method for the synthesis of optically active homoallylamines was developed. Key features of the method include (1) the utilization of naphthylethylamine as both an excellent chiral auxiliary and the amine source, (2) the 1,3-chiral induction of the N-acyliminium ion with high stereoselectivity and high yield, and (3) facile auxiliary removal under mild conditions to liberate N-Cbz-protected homoallylamines. In addition, the total synthesis of the proposed novel tripeptide containing a β-amino acid has been achieved by applying this method.

Original language	English
Pages (from-to)	5920-5923
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	21
DOIs	https://doi.org/10.1021/ol202573s
State	Published - 4 Nov 2011

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abstract = "A highly stereoselective and efficient method for the synthesis of optically active homoallylamines was developed. Key features of the method include (1) the utilization of naphthylethylamine as both an excellent chiral auxiliary and the amine source, (2) the 1,3-chiral induction of the N-acyliminium ion with high stereoselectivity and high yield, and (3) facile auxiliary removal under mild conditions to liberate N-Cbz-protected homoallylamines. In addition, the total synthesis of the proposed novel tripeptide containing a β-amino acid has been achieved by applying this method.",

author = "Suh, {Young Ger} and Jaebong Jang and Hwayoung Yun and Han, {Sae Mi} and Dongyun Shin and Jung, {Jae Kyung} and Jung, {Jong Wha}",

year = "2011",

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doi = "10.1021/ol202573s",

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T1 - Expedient synthesis of chiral homoallylamines via N, O-acetal TMS ethers and its application

AU - Suh, Young Ger

AU - Jang, Jaebong

AU - Yun, Hwayoung

AU - Han, Sae Mi

AU - Shin, Dongyun

AU - Jung, Jae Kyung

AU - Jung, Jong Wha

PY - 2011/11/4

Y1 - 2011/11/4

N2 - A highly stereoselective and efficient method for the synthesis of optically active homoallylamines was developed. Key features of the method include (1) the utilization of naphthylethylamine as both an excellent chiral auxiliary and the amine source, (2) the 1,3-chiral induction of the N-acyliminium ion with high stereoselectivity and high yield, and (3) facile auxiliary removal under mild conditions to liberate N-Cbz-protected homoallylamines. In addition, the total synthesis of the proposed novel tripeptide containing a β-amino acid has been achieved by applying this method.

AB - A highly stereoselective and efficient method for the synthesis of optically active homoallylamines was developed. Key features of the method include (1) the utilization of naphthylethylamine as both an excellent chiral auxiliary and the amine source, (2) the 1,3-chiral induction of the N-acyliminium ion with high stereoselectivity and high yield, and (3) facile auxiliary removal under mild conditions to liberate N-Cbz-protected homoallylamines. In addition, the total synthesis of the proposed novel tripeptide containing a β-amino acid has been achieved by applying this method.

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AN - SCOPUS:80055081522

SN - 1523-7060

VL - 13

SP - 5920

EP - 5923

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Expedient synthesis of chiral homoallylamines via N, O-acetal TMS ethers and its application

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