Nucleophile-selective iodocyclizations: Butyrolactone versus tetrahydrofuran formation

Mark J. Kurth; Richard L. Beard; Marilyn Olmstead; James G. Macmillan

Nucleophile-selective iodocyclizations: Butyrolactone versus tetrahydrofuran formation

Mark J. Kurth, Richard L. Beard, Marilyn Olmstead, James G. Macmillan

Chemistry

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

26 Scopus citations

Abstract

Nucleophile selectivity in the electrophilic cyclization of substrates like 3 has been investigated in the context of efficient chemo- and stereoselective functionalization of 3-hydroxy-2-(2-methylenecyclohexan-1-yl)butyric acids (cf., 6-9) via iodocyclization. In addition, composite nucleophile selectivities for this diastereomeric series were used to probe the reliability of ground-state conformational analysis as an indicator of relative reactivities for the various conformations of 3. The results provide unambiguous evidence for C_1′,C₂,C₃ stereocontrol in these kinetic iodocyclizations.

Original language	English (US)
Pages (from-to)	3712-3717
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	111
Issue number	10
State	Published - 1989

ASJC Scopus subject areas

Chemistry(all)

Fingerprint Dive into the research topics of 'Nucleophile-selective iodocyclizations: Butyrolactone versus tetrahydrofuran formation'. Together they form a unique fingerprint.

Cite this

@article{fad55d20cce948999ef0923885c83cc8,

title = "Nucleophile-selective iodocyclizations: Butyrolactone versus tetrahydrofuran formation",

abstract = "Nucleophile selectivity in the electrophilic cyclization of substrates like 3 has been investigated in the context of efficient chemo- and stereoselective functionalization of 3-hydroxy-2-(2-methylenecyclohexan-1-yl)butyric acids (cf., 6-9) via iodocyclization. In addition, composite nucleophile selectivities for this diastereomeric series were used to probe the reliability of ground-state conformational analysis as an indicator of relative reactivities for the various conformations of 3. The results provide unambiguous evidence for C1′,C2,C3 stereocontrol in these kinetic iodocyclizations.",

author = "Kurth, {Mark J.} and Beard, {Richard L.} and Marilyn Olmstead and Macmillan, {James G.}",

year = "1989",

language = "English (US)",

volume = "111",

pages = "3712--3717",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Nucleophile-selective iodocyclizations

T2 - Butyrolactone versus tetrahydrofuran formation

AU - Kurth, Mark J.

AU - Beard, Richard L.

AU - Olmstead, Marilyn

AU - Macmillan, James G.

PY - 1989

Y1 - 1989

N2 - Nucleophile selectivity in the electrophilic cyclization of substrates like 3 has been investigated in the context of efficient chemo- and stereoselective functionalization of 3-hydroxy-2-(2-methylenecyclohexan-1-yl)butyric acids (cf., 6-9) via iodocyclization. In addition, composite nucleophile selectivities for this diastereomeric series were used to probe the reliability of ground-state conformational analysis as an indicator of relative reactivities for the various conformations of 3. The results provide unambiguous evidence for C1′,C2,C3 stereocontrol in these kinetic iodocyclizations.

AB - Nucleophile selectivity in the electrophilic cyclization of substrates like 3 has been investigated in the context of efficient chemo- and stereoselective functionalization of 3-hydroxy-2-(2-methylenecyclohexan-1-yl)butyric acids (cf., 6-9) via iodocyclization. In addition, composite nucleophile selectivities for this diastereomeric series were used to probe the reliability of ground-state conformational analysis as an indicator of relative reactivities for the various conformations of 3. The results provide unambiguous evidence for C1′,C2,C3 stereocontrol in these kinetic iodocyclizations.

UR - http://www.scopus.com/inward/record.url?scp=0000183056&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000183056&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0000183056

VL - 111

SP - 3712

EP - 3717

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 10

ER -

Nucleophile-selective iodocyclizations: Butyrolactone versus tetrahydrofuran formation

Abstract

ASJC Scopus subject areas

Other files and links

Cite this