Nucleophilic substitution gone awry: A novel cyclopropanation reaction with a surprising stereochemical outcome

Charles J. Torborg; John J. Rabasco; Steven R. Kass

doi:10.1016/0040-4039(95)01192-K

Nucleophilic substitution gone awry: A novel cyclopropanation reaction with a surprising stereochemical outcome

Charles J. Torborg, John J. Rabasco, Steven R. Kass

Chemistry (Twin Cities)

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

2 Scopus citations

Abstract

Lithium triethylborohydride reacts with the triisopropylbenzene sulfonate ester of 2-methoxy-5,5-dimethyl-2-vinyl-3-cyclohexen-1-ol (1) to afford 8-methoxy-6,6-dimethylspiro[2.5]oct-4-ene (3). Labeling studies reveal that this novel cyclopropane forming reaction proceeds with retention of configuration at the newly formed quaternary center.

Original language	English (US)
Pages (from-to)	6025-6028
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	34
DOIs	https://doi.org/10.1016/0040-4039(95)01192-K
State	Published - Aug 21 1995

Keywords

cyclopropane formation
nucleophilic substitution
rearrangement
stereochemistry

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10.1016/0040-4039(95)01192-K

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title = "Nucleophilic substitution gone awry: A novel cyclopropanation reaction with a surprising stereochemical outcome",

abstract = "Lithium triethylborohydride reacts with the triisopropylbenzene sulfonate ester of 2-methoxy-5,5-dimethyl-2-vinyl-3-cyclohexen-1-ol (1) to afford 8-methoxy-6,6-dimethylspiro[2.5]oct-4-ene (3). Labeling studies reveal that this novel cyclopropane forming reaction proceeds with retention of configuration at the newly formed quaternary center.",

keywords = "cyclopropane formation, nucleophilic substitution, rearrangement, stereochemistry",

author = "Torborg, {Charles J.} and Rabasco, {John J.} and Kass, {Steven R.}",

year = "1995",

month = aug,

day = "21",

doi = "10.1016/0040-4039(95)01192-K",

language = "English (US)",

volume = "36",

pages = "6025--6028",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "34",

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TY - JOUR

T1 - Nucleophilic substitution gone awry

T2 - A novel cyclopropanation reaction with a surprising stereochemical outcome

AU - Torborg, Charles J.

AU - Rabasco, John J.

AU - Kass, Steven R.

PY - 1995/8/21

Y1 - 1995/8/21

N2 - Lithium triethylborohydride reacts with the triisopropylbenzene sulfonate ester of 2-methoxy-5,5-dimethyl-2-vinyl-3-cyclohexen-1-ol (1) to afford 8-methoxy-6,6-dimethylspiro[2.5]oct-4-ene (3). Labeling studies reveal that this novel cyclopropane forming reaction proceeds with retention of configuration at the newly formed quaternary center.

AB - Lithium triethylborohydride reacts with the triisopropylbenzene sulfonate ester of 2-methoxy-5,5-dimethyl-2-vinyl-3-cyclohexen-1-ol (1) to afford 8-methoxy-6,6-dimethylspiro[2.5]oct-4-ene (3). Labeling studies reveal that this novel cyclopropane forming reaction proceeds with retention of configuration at the newly formed quaternary center.

KW - cyclopropane formation

KW - nucleophilic substitution

KW - rearrangement

KW - stereochemistry

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U2 - 10.1016/0040-4039(95)01192-K

DO - 10.1016/0040-4039(95)01192-K

M3 - Article

AN - SCOPUS:0029165479

VL - 36

SP - 6025

EP - 6028

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 34

ER -