Stereospecific syntheses of macrobicyclic polyethers with carbon bridgeheads from chiral glycerol derivatives

Billy L. Allwood; Steven E. Fuller; Peter C Y K Ning; Alexandra M Z Slawin; J. Fraser Stoddart; David J. Williams

doi:10.1039/C39840001356

Stereospecific syntheses of macrobicyclic polyethers with carbon bridgeheads from chiral glycerol derivatives

Billy L. Allwood, Steven E. Fuller, Peter C Y K Ning, Alexandra M Z Slawin, J. Fraser Stoddart, David J. Williams

Chemistry

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Abstract

The [3.3.3]cryptand (3), prepared stereospecifically from 2,3-O-isopropylidene-D-glycerol d-(1) and 2,3-di-O-benzyl-L- glycerol L-(2), has been separated chromatographically at −5°C into slowly interconverting in-inii-(3) and out-out oo-(3) conformational diastereoisomers [ΔG^‡_ii→oo = ca. 24 kcal moh⁻¹ (1 kcal = 4.184 kJ) in CD₃COCD₃ at +38°C]; an X-ray structural analysis has shown (3) to form a crystalline 1:1 complex with Ba(SCN)₂ in which the Ba²⁺ ion is encapsulated by oo-(3) and the two SCN− ions in an 11-co-ordinate manner.

Original language	English (US)
Pages (from-to)	1356-1360
Number of pages	5
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	20
DOIs	https://doi.org/10.1039/C39840001356
State	Published - 1984

ASJC Scopus subject areas

Molecular Medicine

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title = "Stereospecific syntheses of macrobicyclic polyethers with carbon bridgeheads from chiral glycerol derivatives",

abstract = "The [3.3.3]cryptand (3), prepared stereospecifically from 2,3-O-isopropylidene-D-glycerol d-(1) and 2,3-di-O-benzyl-L- glycerol L-(2), has been separated chromatographically at −5°C into slowly interconverting in-inii-(3) and out-out oo-(3) conformational diastereoisomers [ΔG‡ii→oo = ca. 24 kcal moh−1 (1 kcal = 4.184 kJ) in CD3COCD3 at +38°C]; an X-ray structural analysis has shown (3) to form a crystalline 1:1 complex with Ba(SCN)2 in which the Ba2+ ion is encapsulated by oo-(3) and the two SCN− ions in an 11-co-ordinate manner.",

author = "Allwood, {Billy L.} and Fuller, {Steven E.} and Ning, {Peter C Y K} and Slawin, {Alexandra M Z} and Stoddart, {J. Fraser} and Williams, {David J.}",

year = "1984",

doi = "10.1039/C39840001356",

language = "English (US)",

pages = "1356--1360",

journal = "Journal of the Chemical Society, Chemical Communications",

issn = "0022-4936",

publisher = "Chemical Society",

number = "20",

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TY - JOUR

T1 - Stereospecific syntheses of macrobicyclic polyethers with carbon bridgeheads from chiral glycerol derivatives

AU - Allwood, Billy L.

AU - Fuller, Steven E.

AU - Ning, Peter C Y K

AU - Slawin, Alexandra M Z

AU - Stoddart, J. Fraser

AU - Williams, David J.

PY - 1984

Y1 - 1984

N2 - The [3.3.3]cryptand (3), prepared stereospecifically from 2,3-O-isopropylidene-D-glycerol d-(1) and 2,3-di-O-benzyl-L- glycerol L-(2), has been separated chromatographically at −5°C into slowly interconverting in-inii-(3) and out-out oo-(3) conformational diastereoisomers [ΔG‡ii→oo = ca. 24 kcal moh−1 (1 kcal = 4.184 kJ) in CD3COCD3 at +38°C]; an X-ray structural analysis has shown (3) to form a crystalline 1:1 complex with Ba(SCN)2 in which the Ba2+ ion is encapsulated by oo-(3) and the two SCN− ions in an 11-co-ordinate manner.

AB - The [3.3.3]cryptand (3), prepared stereospecifically from 2,3-O-isopropylidene-D-glycerol d-(1) and 2,3-di-O-benzyl-L- glycerol L-(2), has been separated chromatographically at −5°C into slowly interconverting in-inii-(3) and out-out oo-(3) conformational diastereoisomers [ΔG‡ii→oo = ca. 24 kcal moh−1 (1 kcal = 4.184 kJ) in CD3COCD3 at +38°C]; an X-ray structural analysis has shown (3) to form a crystalline 1:1 complex with Ba(SCN)2 in which the Ba2+ ion is encapsulated by oo-(3) and the two SCN− ions in an 11-co-ordinate manner.

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JF - Journal of the Chemical Society, Chemical Communications

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ER -

Stereospecific syntheses of macrobicyclic polyethers with carbon bridgeheads from chiral glycerol derivatives

Abstract

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