The diastereoselective formation of tetraalkoxy[4]resorcinarenes derived from (-)-(2R)-2-methoxy-2-phenylethanol and proof of absolute configurations

Philip C. Bulman Page; Yohan Chan; Harry Heaney; Matthew J. McGrath; Eduardo Moreno

doi:10.1002/ejoc.201100733

The diastereoselective formation of tetraalkoxy[4]resorcinarenes derived from (-)-(2R)-2-methoxy-2-phenylethanol and proof of absolute configurations

Philip C. Bulman Page, Yohan Chan, Harry Heaney, Matthew J. McGrath, Eduardo Moreno

Chemistry of Materials and Catalysis

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

3 Citations (Scopus)

Abstract

The preparation of optically pure (-)-3-[(2R)-2-methoxy-2-phenylethoxy] phenol from resorcinol monobenzoate and its conversion into diastereoisomeric tetraalkoxyresorcin[4]arenes together with proof of the absolute configurations of the products is reported. The results of the study indicate that diastereoselective ring closure of linear tetrameric intermediates is controlled by the steric demand of the alkyl group in the precursor 3-alkoxyphenol.

Original language	English
Pages (from-to)	5347-5354
Number of pages	8
Journal	European Journal of Organic Chemistry
Volume	2011
Issue number	27
DOIs	https://doi.org/10.1002/ejoc.201100733
Publication status	Published - Sep 2011

Access to Document

10.1002/ejoc.201100733

Cite this

@article{e833339c43fb4a0cb731b01fdc16fd30,

title = "The diastereoselective formation of tetraalkoxy[4]resorcinarenes derived from (-)-(2R)-2-methoxy-2-phenylethanol and proof of absolute configurations",

abstract = "The preparation of optically pure (-)-3-[(2R)-2-methoxy-2-phenylethoxy] phenol from resorcinol monobenzoate and its conversion into diastereoisomeric tetraalkoxyresorcin[4]arenes together with proof of the absolute configurations of the products is reported. The results of the study indicate that diastereoselective ring closure of linear tetrameric intermediates is controlled by the steric demand of the alkyl group in the precursor 3-alkoxyphenol.",

author = "{Bulman Page}, {Philip C.} and Yohan Chan and Harry Heaney and McGrath, {Matthew J.} and Eduardo Moreno",

year = "2011",

month = sep,

doi = "10.1002/ejoc.201100733",

language = "English",

volume = "2011",

pages = "5347--5354",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley",

number = "27",

}

The diastereoselective formation of tetraalkoxy[4]resorcinarenes derived from (-)-(2R)-2-methoxy-2-phenylethanol and proof of absolute configurations. / Bulman Page, Philip C.; Chan, Yohan; Heaney, Harry; McGrath, Matthew J.; Moreno, Eduardo.

In: European Journal of Organic Chemistry, Vol. 2011, No. 27, 09.2011, p. 5347-5354.

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

TY - JOUR

T1 - The diastereoselective formation of tetraalkoxy[4]resorcinarenes derived from (-)-(2R)-2-methoxy-2-phenylethanol and proof of absolute configurations

AU - Bulman Page, Philip C.

AU - Chan, Yohan

AU - Heaney, Harry

AU - McGrath, Matthew J.

AU - Moreno, Eduardo

PY - 2011/9

Y1 - 2011/9

N2 - The preparation of optically pure (-)-3-[(2R)-2-methoxy-2-phenylethoxy] phenol from resorcinol monobenzoate and its conversion into diastereoisomeric tetraalkoxyresorcin[4]arenes together with proof of the absolute configurations of the products is reported. The results of the study indicate that diastereoselective ring closure of linear tetrameric intermediates is controlled by the steric demand of the alkyl group in the precursor 3-alkoxyphenol.

AB - The preparation of optically pure (-)-3-[(2R)-2-methoxy-2-phenylethoxy] phenol from resorcinol monobenzoate and its conversion into diastereoisomeric tetraalkoxyresorcin[4]arenes together with proof of the absolute configurations of the products is reported. The results of the study indicate that diastereoselective ring closure of linear tetrameric intermediates is controlled by the steric demand of the alkyl group in the precursor 3-alkoxyphenol.

U2 - 10.1002/ejoc.201100733

DO - 10.1002/ejoc.201100733

M3 - Article

VL - 2011

SP - 5347

EP - 5354

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 27

ER -