Concise synthesis of C2-symmetric trans-2,5-dioxymethylpyrrolidine derivatives by novel cyclization

Seiichi Takano; Minoru Moriya; Yoshiharu Iwabuchi; Kunio Ogasawara

doi:10.1016/S0040-4039(01)80661-4

Concise synthesis of C₂-symmetric trans-2,5-dioxymethylpyrrolidine derivatives by novel cyclization

Seiichi Takano, Minoru Moriya, Yoshiharu Iwabuchi, Kunio Ogasawara

PHA - Molecular Pharmaceutical Science

Tohoku University

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

32 Citations (Scopus)

Abstract

Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-benzyloxymethylpyrroliaine stereoselectively in a single step. The product was converted into C₂-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.

Original language	English
Pages (from-to)	3805-3806
Number of pages	2
Journal	Tetrahedron Letters
Volume	30
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4039(01)80661-4
Publication status	Published - 1989

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/S0040-4039(01)80661-4

Cite this

@article{ae273d1a9af943269afd0f132a31bbee,

title = "Concise synthesis of C2-symmetric trans-2,5-dioxymethylpyrrolidine derivatives by novel cyclization",

abstract = "Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-benzyloxymethylpyrroliaine stereoselectively in a single step. The product was converted into C2-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.",

author = "Seiichi Takano and Minoru Moriya and Yoshiharu Iwabuchi and Kunio Ogasawara",

year = "1989",

doi = "10.1016/S0040-4039(01)80661-4",

language = "English",

volume = "30",

pages = "3805--3806",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "29",

}

TY - JOUR

T1 - Concise synthesis of C2-symmetric trans-2,5-dioxymethylpyrrolidine derivatives by novel cyclization

AU - Takano, Seiichi

AU - Moriya, Minoru

AU - Iwabuchi, Yoshiharu

AU - Ogasawara, Kunio

PY - 1989

Y1 - 1989

N2 - Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-benzyloxymethylpyrroliaine stereoselectively in a single step. The product was converted into C2-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.

AB - Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-benzyloxymethylpyrroliaine stereoselectively in a single step. The product was converted into C2-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.

UR - http://www.scopus.com/inward/record.url?scp=0000625840&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000625840&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)80661-4

DO - 10.1016/S0040-4039(01)80661-4

M3 - Article

AN - SCOPUS:0000625840

SN - 0040-4039

VL - 30

SP - 3805

EP - 3806

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Concise synthesis of C₂-symmetric trans-2,5-dioxymethylpyrrolidine derivatives by novel cyclization

Abstract

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this