Stereocontrolled synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4- diaminocyclopentanols

Yousheng Guan, Mark Green, Donald E. Bergstrom

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Cis-syn and cis-anti-3,4-diaminocyclopentanols have been synthesized from cyclopentadiene in eight steps. The key transformations involved construction of benzyl ether protected cis-diazidocyclopentanols, and sequential reduction and hydrogenolysis to the unprotected diaminocyclopentanols.

Original languageEnglish (US)
Pages (from-to)426-428
Number of pages3
JournalSynlett
Issue number4
StatePublished - 1999
Externally publishedYes

Fingerprint

Cyclopentanes
Hydrogenolysis
Ether

Keywords

  • Debenzylation
  • Diaminocyclopentanol
  • Diazide reduction
  • Stereocontrolled synthesis
  • Vicinal diamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereocontrolled synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4- diaminocyclopentanols. / Guan, Yousheng; Green, Mark; Bergstrom, Donald E.

In: Synlett, No. 4, 1999, p. 426-428.

Research output: Contribution to journalArticle

Guan, Yousheng ; Green, Mark ; Bergstrom, Donald E. / Stereocontrolled synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4- diaminocyclopentanols. In: Synlett. 1999 ; No. 4. pp. 426-428.
@article{a5ee3d8febd74ed7a7b73f9179347562,
title = "Stereocontrolled synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4- diaminocyclopentanols",
abstract = "Cis-syn and cis-anti-3,4-diaminocyclopentanols have been synthesized from cyclopentadiene in eight steps. The key transformations involved construction of benzyl ether protected cis-diazidocyclopentanols, and sequential reduction and hydrogenolysis to the unprotected diaminocyclopentanols.",
keywords = "Debenzylation, Diaminocyclopentanol, Diazide reduction, Stereocontrolled synthesis, Vicinal diamine",
author = "Yousheng Guan and Mark Green and Bergstrom, {Donald E.}",
year = "1999",
language = "English (US)",
pages = "426--428",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "4",

}

TY - JOUR

T1 - Stereocontrolled synthesis of (1R,3R,4S)- and (1S,3R,4S)-3,4- diaminocyclopentanols

AU - Guan, Yousheng

AU - Green, Mark

AU - Bergstrom, Donald E.

PY - 1999

Y1 - 1999

N2 - Cis-syn and cis-anti-3,4-diaminocyclopentanols have been synthesized from cyclopentadiene in eight steps. The key transformations involved construction of benzyl ether protected cis-diazidocyclopentanols, and sequential reduction and hydrogenolysis to the unprotected diaminocyclopentanols.

AB - Cis-syn and cis-anti-3,4-diaminocyclopentanols have been synthesized from cyclopentadiene in eight steps. The key transformations involved construction of benzyl ether protected cis-diazidocyclopentanols, and sequential reduction and hydrogenolysis to the unprotected diaminocyclopentanols.

KW - Debenzylation

KW - Diaminocyclopentanol

KW - Diazide reduction

KW - Stereocontrolled synthesis

KW - Vicinal diamine

UR - http://www.scopus.com/inward/record.url?scp=0032920003&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032920003&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0032920003

SP - 426

EP - 428

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 4

ER -