A highly effective asymmetric synthesis of α-hydroxy acids by alkylation of chiral n-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine

Masayuki Enomoto; Yoshio Ito; Tsutomu Katsuki; Masaru Yamaguchi

doi:10.1016/S0040-4039(00)94889-5

A highly effective asymmetric synthesis of α-hydroxy acids by alkylation of chiral n-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine

Masayuki Enomoto, Yoshio Ito, Tsutomu Katsuki, Masaru Yamaguchi

Center of Environment and Safety

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

59 Citations (Scopus)

Abstract

Alkylation of lithiated N-(benzyloxyacetyl)-trans-2,5-bis(mehtoxyymethoxymethyl)- pyrrolidine proceeded with high stereoselectivity (≥96% de) and subsequent transformations of the alkylated products gave synthetically useful α-benzyloxy acids or α-hydroxy acids of high enantiomeric purity.

Original language	English
Pages (from-to)	1343-1344
Number of pages	2
Journal	Tetrahedron Letters
Volume	26
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(00)94889-5
Publication status	Published - 1985

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)94889-5

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title = "A highly effective asymmetric synthesis of α-hydroxy acids by alkylation of chiral n-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine",

abstract = "Alkylation of lithiated N-(benzyloxyacetyl)-trans-2,5-bis(mehtoxyymethoxymethyl)- pyrrolidine proceeded with high stereoselectivity (≥96% de) and subsequent transformations of the alkylated products gave synthetically useful α-benzyloxy acids or α-hydroxy acids of high enantiomeric purity.",

author = "Masayuki Enomoto and Yoshio Ito and Tsutomu Katsuki and Masaru Yamaguchi",

year = "1985",

doi = "10.1016/S0040-4039(00)94889-5",

language = "English",

volume = "26",

pages = "1343--1344",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "10",

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T1 - A highly effective asymmetric synthesis of α-hydroxy acids by alkylation of chiral n-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine

AU - Enomoto, Masayuki

AU - Ito, Yoshio

AU - Katsuki, Tsutomu

AU - Yamaguchi, Masaru

PY - 1985

Y1 - 1985

N2 - Alkylation of lithiated N-(benzyloxyacetyl)-trans-2,5-bis(mehtoxyymethoxymethyl)- pyrrolidine proceeded with high stereoselectivity (≥96% de) and subsequent transformations of the alkylated products gave synthetically useful α-benzyloxy acids or α-hydroxy acids of high enantiomeric purity.

AB - Alkylation of lithiated N-(benzyloxyacetyl)-trans-2,5-bis(mehtoxyymethoxymethyl)- pyrrolidine proceeded with high stereoselectivity (≥96% de) and subsequent transformations of the alkylated products gave synthetically useful α-benzyloxy acids or α-hydroxy acids of high enantiomeric purity.

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U2 - 10.1016/S0040-4039(00)94889-5

DO - 10.1016/S0040-4039(00)94889-5

M3 - Article

AN - SCOPUS:46549104335

SN - 0040-4039

VL - 26

SP - 1343

EP - 1344

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

A highly effective asymmetric synthesis of α-hydroxy acids by alkylation of chiral n-(benzyloxyacetyl)-trans-2,5-bis(methoxymethoxymethyl)pyrrolidine

Abstract

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