Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

Jennifer R. Krumper, Walter A. Salamant, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.

Original languageEnglish (US)
Pages (from-to)4907-4910
Number of pages4
JournalOrganic Letters
Volume10
Issue number21
DOIs
StatePublished - 2008

Fingerprint

Stereoselectivity
acetals
Lewis Acids
Acetals
Nucleophiles
nucleophiles
erosion
Erosion
Substitution reactions
substitutes
inversions
continuums
acids
thresholds

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Continuum of mechanisms for nucleophilic substitutions of cyclic acetals. / Krumper, Jennifer R.; Salamant, Walter A.; Woerpel, Keith.

In: Organic Letters, Vol. 10, No. 21, 2008, p. 4907-4910.

Research output: Contribution to journalArticle

Krumper, Jennifer R. ; Salamant, Walter A. ; Woerpel, Keith. / Continuum of mechanisms for nucleophilic substitutions of cyclic acetals. In: Organic Letters. 2008 ; Vol. 10, No. 21. pp. 4907-4910.
@article{aca609fa146f4731b8387c70fdb6452e,
title = "Continuum of mechanisms for nucleophilic substitutions of cyclic acetals",
abstract = "(Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.",
author = "Krumper, {Jennifer R.} and Salamant, {Walter A.} and Keith Woerpel",
year = "2008",
doi = "10.1021/ol8019956",
language = "English (US)",
volume = "10",
pages = "4907--4910",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "21",

}

TY - JOUR

T1 - Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

AU - Krumper, Jennifer R.

AU - Salamant, Walter A.

AU - Woerpel, Keith

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.

AB - (Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.

UR - http://www.scopus.com/inward/record.url?scp=58149154432&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=58149154432&partnerID=8YFLogxK

U2 - 10.1021/ol8019956

DO - 10.1021/ol8019956

M3 - Article

C2 - 18844363

AN - SCOPUS:58149154432

VL - 10

SP - 4907

EP - 4910

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 21

ER -