Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction

Atsushi Umehara; Takuya Kanemitsu; Kazuhiro Nagata; Takashi Itoh

doi:10.1055/s-0031-1290316

Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction

Atsushi Umehara, Takuya Kanemitsu, Kazuhiro Nagata, Takashi Itoh

LIF - Molecular and Chemical Life Science

Showa University

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

11 Citations (Scopus)

Abstract

L-tert-Leucine was found to be an effective organocatalyst for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones with high syn selectivity (syn/anti = 16:1) and enantioselectivity (up to 95% ee).

Original language	English
Pages (from-to)	453-457
Number of pages	5
Journal	Synlett
Issue number	3
DOIs	https://doi.org/10.1055/s-0031-1290316
Publication status	Published - 2012

Keywords

aldol reaction
amino acids
asymmetric synthesis
chloroacetone
organocatalysis

Access to Document

10.1055/s-0031-1290316

Cite this

@article{5efabd12f22b414d8c6c5a6123a6fe21,

title = "Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction",

abstract = "L-tert-Leucine was found to be an effective organocatalyst for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones with high syn selectivity (syn/anti = 16:1) and enantioselectivity (up to 95% ee).",

keywords = "aldol reaction, amino acids, asymmetric synthesis, chloroacetone, organocatalysis",

author = "Atsushi Umehara and Takuya Kanemitsu and Kazuhiro Nagata and Takashi Itoh",

year = "2012",

doi = "10.1055/s-0031-1290316",

language = "English",

pages = "453--457",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "3",

}

TY - JOUR

T1 - Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction

AU - Umehara, Atsushi

AU - Kanemitsu, Takuya

AU - Nagata, Kazuhiro

AU - Itoh, Takashi

PY - 2012

Y1 - 2012

N2 - L-tert-Leucine was found to be an effective organocatalyst for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones with high syn selectivity (syn/anti = 16:1) and enantioselectivity (up to 95% ee).

AB - L-tert-Leucine was found to be an effective organocatalyst for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones with high syn selectivity (syn/anti = 16:1) and enantioselectivity (up to 95% ee).

KW - aldol reaction

KW - amino acids

KW - asymmetric synthesis

KW - chloroacetone

KW - organocatalysis

UR - http://www.scopus.com/inward/record.url?scp=84856590736&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84856590736&partnerID=8YFLogxK

U2 - 10.1055/s-0031-1290316

DO - 10.1055/s-0031-1290316

M3 - Article

AN - SCOPUS:84856590736

SN - 0936-5214

SP - 453

EP - 457

JO - Synlett

JF - Synlett

IS - 3

ER -

Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this