Prevalence of Eight-membered hydrogen-bonded rings in some bis(cyclobutane) β-dipeptides including residues with trans stereochemistry

Elisabeth Torres; Esther Gorrea; Eric Da Silva; Pau Nolis; Vicenç Branchadell; Rosa M. Ortuño

doi:10.1021/ol900636w

Prevalence of Eight-membered hydrogen-bonded rings in some bis(cyclobutane) β-dipeptides including residues with trans stereochemistry

Elisabeth Torres, Esther Gorrea, Eric Da Silva, Pau Nolis, Vicenç Branchadell, Rosa M. Ortuño

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

40 Citations (Scopus)

Abstract

Three new bis(cyclobutane) β-dipeptides have been synthesized from appropriate derivatives of cis- and trans-2-aminocyclobutane-1-carboxylic acid, respectively. The predominance of eight-membered hydrogen-bonded rings has been manifested for (trans,trans)- and (trans,cis)-β- dipeptides while the formation of six-membered rings is preferred for the (cis,trans)- β-dipeptide similarly to the previously described (cis,cis)-diastereomer. © 2009 American Chemical Society.

Original language	English
Pages (from-to)	2301-2304
Journal	Organic Letters
Volume	11
Issue number	11
DOIs	https://doi.org/10.1021/ol900636w
Publication status	Published - 4 Jun 2009

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10.1021/ol900636w

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title = "Prevalence of Eight-membered hydrogen-bonded rings in some bis(cyclobutane) β-dipeptides including residues with trans stereochemistry",

abstract = "Three new bis(cyclobutane) β-dipeptides have been synthesized from appropriate derivatives of cis- and trans-2-aminocyclobutane-1-carboxylic acid, respectively. The predominance of eight-membered hydrogen-bonded rings has been manifested for (trans,trans)- and (trans,cis)-β- dipeptides while the formation of six-membered rings is preferred for the (cis,trans)- β-dipeptide similarly to the previously described (cis,cis)-diastereomer. {\textcopyright} 2009 American Chemical Society.",

author = "Elisabeth Torres and Esther Gorrea and {Da Silva}, Eric and Pau Nolis and Vicen{\c c} Branchadell and Ortu{\~n}o, {Rosa M.}",

year = "2009",

month = jun,

day = "4",

doi = "10.1021/ol900636w",

language = "English",

volume = "11",

pages = "2301--2304",

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}

Prevalence of Eight-membered hydrogen-bonded rings in some bis(cyclobutane) β-dipeptides including residues with trans stereochemistry. / Torres, Elisabeth; Gorrea, Esther; Da Silva, Eric; Nolis, Pau ; Branchadell, Vicenç ; Ortuño, Rosa M.

In: Organic Letters, Vol. 11, No. 11, 04.06.2009, p. 2301-2304.

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

TY - JOUR

T1 - Prevalence of Eight-membered hydrogen-bonded rings in some bis(cyclobutane) β-dipeptides including residues with trans stereochemistry

AU - Torres, Elisabeth

AU - Gorrea, Esther

AU - Da Silva, Eric

AU - Nolis, Pau

AU - Branchadell, Vicenç

AU - Ortuño, Rosa M.

PY - 2009/6/4

Y1 - 2009/6/4

N2 - Three new bis(cyclobutane) β-dipeptides have been synthesized from appropriate derivatives of cis- and trans-2-aminocyclobutane-1-carboxylic acid, respectively. The predominance of eight-membered hydrogen-bonded rings has been manifested for (trans,trans)- and (trans,cis)-β- dipeptides while the formation of six-membered rings is preferred for the (cis,trans)- β-dipeptide similarly to the previously described (cis,cis)-diastereomer. © 2009 American Chemical Society.

AB - Three new bis(cyclobutane) β-dipeptides have been synthesized from appropriate derivatives of cis- and trans-2-aminocyclobutane-1-carboxylic acid, respectively. The predominance of eight-membered hydrogen-bonded rings has been manifested for (trans,trans)- and (trans,cis)-β- dipeptides while the formation of six-membered rings is preferred for the (cis,trans)- β-dipeptide similarly to the previously described (cis,cis)-diastereomer. © 2009 American Chemical Society.

U2 - 10.1021/ol900636w

DO - 10.1021/ol900636w

M3 - Article

VL - 11

SP - 2301

EP - 2304

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