Lewis acid catalysis of second-generation metallosalen complexes: An explanation for stereochemistry of asymmetric hetero Diels-Alder reaction

Jun Mihara, Kohsuke Aikawa, Tatsuya Uchida, Ryo Irie, Tsutomu Katsuki

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Chloro nitrosyl (R,S)-(salen)ruthenium(II) complex served as a good catalyst for asymmetric hetero Diels-Alder (HDA) reaction of Danishefsky's diene with a wide variety of aldehydes. In contrast with this, (R,R)-(salen)-chromium(III) and -manganese(III) complexes well catalyze HDA reaction of simple aldehydes, while (R,S)-(salen)-chromium(III) and-manganese(III) complexes better catalyze HDA reaction of aldehydes bearing a precoordinating group. These features of metallosalen-catalyzed HDA reactions were rationalized by assuming that HDA reaction of aldehydes beating a precoordinating group would proceed through aldehyde-metallosalen complex which takes cis-β-structure.

Original languageEnglish
Pages (from-to)395-404
Number of pages10
JournalHeterocycles
Volume54
Issue number1
Publication statusPublished - Jan 1 2001

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Lewis Acids
Stereochemistry
Cycloaddition Reaction
Catalysis
Aldehydes
Chromium
Manganese
Bearings (structural)
Ruthenium
Catalysts
disalicylaldehyde ethylenediamine

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Lewis acid catalysis of second-generation metallosalen complexes : An explanation for stereochemistry of asymmetric hetero Diels-Alder reaction. / Mihara, Jun; Aikawa, Kohsuke; Uchida, Tatsuya; Irie, Ryo; Katsuki, Tsutomu.

In: Heterocycles, Vol. 54, No. 1, 01.01.2001, p. 395-404.

Research output: Contribution to journalArticle

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