The stereoselective synthesis of α-amino aldols starting from terminal alkynes

Tomoya Miura; Takayuki Nakamuro; Kentaro Hiraga; Masahiro Murakami

doi:10.1039/c4cc04786a

The stereoselective synthesis of α-amino aldols starting from terminal alkynes

Tomoya Miura, Takayuki Nakamuro, Kentaro Hiraga, Masahiro Murakami

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

38 Citations (Scopus)

Abstract

A new procedure for the stereoselective synthesis of syn α-amino β-oxy ketones is reported. It consists of two steps; in the first step, α-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl₄-mediated Mukaiyama aldol reaction with aldehydes to produce α-amino β-oxy ketones with excellent syn-selectivity.

Original language	English
Pages (from-to)	10474-10477
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	72
DOIs	https://doi.org/10.1039/c4cc04786a
Publication status	Published - Aug 12 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "The stereoselective synthesis of α-amino aldols starting from terminal alkynes",

abstract = "A new procedure for the stereoselective synthesis of syn α-amino β-oxy ketones is reported. It consists of two steps; in the first step, α-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl4-mediated Mukaiyama aldol reaction with aldehydes to produce α-amino β-oxy ketones with excellent syn-selectivity.",

author = "Tomoya Miura and Takayuki Nakamuro and Kentaro Hiraga and Masahiro Murakami",

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T1 - The stereoselective synthesis of α-amino aldols starting from terminal alkynes

AU - Miura, Tomoya

AU - Nakamuro, Takayuki

AU - Hiraga, Kentaro

AU - Murakami, Masahiro

PY - 2014/8/12

Y1 - 2014/8/12

N2 - A new procedure for the stereoselective synthesis of syn α-amino β-oxy ketones is reported. It consists of two steps; in the first step, α-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl4-mediated Mukaiyama aldol reaction with aldehydes to produce α-amino β-oxy ketones with excellent syn-selectivity.

AB - A new procedure for the stereoselective synthesis of syn α-amino β-oxy ketones is reported. It consists of two steps; in the first step, α-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl4-mediated Mukaiyama aldol reaction with aldehydes to produce α-amino β-oxy ketones with excellent syn-selectivity.

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JO - Chemical Communications

JF - Chemical Communications

IS - 72

ER -

The stereoselective synthesis of α-amino aldols starting from terminal alkynes

Abstract

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