2.19 Selected Diastereoselective Reactions: Electrocyclizations

E. L. Myers, Dirk Trauner

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

Electrocyclizations provide some of the most impressive examples of diastereoselectivity in synthesis. This is due to the high level of stereochemical control exerted by the conservation of orbital symmetry. Herein, the authors show how electrocyclizations can be used to synthesize stereochemically interesting four- to eight-membered rings as well as bicyclic ring systems using electrocyclizations and electrocyclization cascades. Both thermal and photochemical reactions are covered and substrates containing heteroatoms are discussed along with all-carbon systems.

Original languageEnglish (US)
Title of host publicationComprehensive Chirality
PublisherElsevier Ltd
Pages563-606
Number of pages44
Volume2
ISBN (Print)9780080951683
DOIs
StatePublished - Sep 2012

Fingerprint

Photochemical reactions
Conservation
Carbon
Substrates
Hot Temperature

Keywords

  • Cascade reactions
  • Electrocyclic reaction
  • Electrocyclic ring opening
  • Electrocyclization
  • Woodward-Hoffmann rules

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Myers, E. L., & Trauner, D. (2012). 2.19 Selected Diastereoselective Reactions: Electrocyclizations. In Comprehensive Chirality (Vol. 2, pp. 563-606). Elsevier Ltd. https://doi.org/10.1016/B978-0-08-095167-6.00212-3

2.19 Selected Diastereoselective Reactions : Electrocyclizations. / Myers, E. L.; Trauner, Dirk.

Comprehensive Chirality. Vol. 2 Elsevier Ltd, 2012. p. 563-606.

Research output: Chapter in Book/Report/Conference proceedingChapter

Myers, EL & Trauner, D 2012, 2.19 Selected Diastereoselective Reactions: Electrocyclizations. in Comprehensive Chirality. vol. 2, Elsevier Ltd, pp. 563-606. https://doi.org/10.1016/B978-0-08-095167-6.00212-3
Myers EL, Trauner D. 2.19 Selected Diastereoselective Reactions: Electrocyclizations. In Comprehensive Chirality. Vol. 2. Elsevier Ltd. 2012. p. 563-606 https://doi.org/10.1016/B978-0-08-095167-6.00212-3
Myers, E. L. ; Trauner, Dirk. / 2.19 Selected Diastereoselective Reactions : Electrocyclizations. Comprehensive Chirality. Vol. 2 Elsevier Ltd, 2012. pp. 563-606
@inbook{e66fe8b5ebd946779e8301f495f2e395,
title = "2.19 Selected Diastereoselective Reactions: Electrocyclizations",
abstract = "Electrocyclizations provide some of the most impressive examples of diastereoselectivity in synthesis. This is due to the high level of stereochemical control exerted by the conservation of orbital symmetry. Herein, the authors show how electrocyclizations can be used to synthesize stereochemically interesting four- to eight-membered rings as well as bicyclic ring systems using electrocyclizations and electrocyclization cascades. Both thermal and photochemical reactions are covered and substrates containing heteroatoms are discussed along with all-carbon systems.",
keywords = "Cascade reactions, Electrocyclic reaction, Electrocyclic ring opening, Electrocyclization, Woodward-Hoffmann rules",
author = "Myers, {E. L.} and Dirk Trauner",
year = "2012",
month = "9",
doi = "10.1016/B978-0-08-095167-6.00212-3",
language = "English (US)",
isbn = "9780080951683",
volume = "2",
pages = "563--606",
booktitle = "Comprehensive Chirality",
publisher = "Elsevier Ltd",

}

TY - CHAP

T1 - 2.19 Selected Diastereoselective Reactions

T2 - Electrocyclizations

AU - Myers, E. L.

AU - Trauner, Dirk

PY - 2012/9

Y1 - 2012/9

N2 - Electrocyclizations provide some of the most impressive examples of diastereoselectivity in synthesis. This is due to the high level of stereochemical control exerted by the conservation of orbital symmetry. Herein, the authors show how electrocyclizations can be used to synthesize stereochemically interesting four- to eight-membered rings as well as bicyclic ring systems using electrocyclizations and electrocyclization cascades. Both thermal and photochemical reactions are covered and substrates containing heteroatoms are discussed along with all-carbon systems.

AB - Electrocyclizations provide some of the most impressive examples of diastereoselectivity in synthesis. This is due to the high level of stereochemical control exerted by the conservation of orbital symmetry. Herein, the authors show how electrocyclizations can be used to synthesize stereochemically interesting four- to eight-membered rings as well as bicyclic ring systems using electrocyclizations and electrocyclization cascades. Both thermal and photochemical reactions are covered and substrates containing heteroatoms are discussed along with all-carbon systems.

KW - Cascade reactions

KW - Electrocyclic reaction

KW - Electrocyclic ring opening

KW - Electrocyclization

KW - Woodward-Hoffmann rules

UR - http://www.scopus.com/inward/record.url?scp=84902435073&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84902435073&partnerID=8YFLogxK

U2 - 10.1016/B978-0-08-095167-6.00212-3

DO - 10.1016/B978-0-08-095167-6.00212-3

M3 - Chapter

AN - SCOPUS:84902435073

SN - 9780080951683

VL - 2

SP - 563

EP - 606

BT - Comprehensive Chirality

PB - Elsevier Ltd

ER -