Kinetic resolution of secondary alcohols by chiral dmap derivatives prepared by the Ugi multicomponent reaction

Hiroki Mandai, Shunsuke Irie, Masaru Akehi, Kazunobu Yuri, Masaaki Yoden, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The kinetic resolution of secondary alcohols was examined by new chiral DMAP derivatives, which can readily be prepared by the Ugi multicomponent reaction in a one-pot operation. The initial screening of DMAP derivatives indicated that the catalyst bearing L-valine with an S configuration at the a-position of amide showed the best stereoselectivity factor. After the reaction conditions were optimized with (S,S)-4a in the kinetic resolution of secondary alcohols, various acyclic and cyclic secondary alcohols could be resolved with an s -factor of up to 12.

Original languageEnglish
Pages (from-to)329-340
Number of pages12
JournalHeterocycles
Volume87
Issue number2
DOIs
Publication statusPublished - 2013

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Alcohols
Derivatives
Kinetics
Bearings (structural)
Stereoselectivity
Valine
Amides
Screening
Catalysts

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Kinetic resolution of secondary alcohols by chiral dmap derivatives prepared by the Ugi multicomponent reaction. / Mandai, Hiroki; Irie, Shunsuke; Akehi, Masaru; Yuri, Kazunobu; Yoden, Masaaki; Mitsudo, Koichi; Suga, Seiji.

In: Heterocycles, Vol. 87, No. 2, 2013, p. 329-340.

Research output: Contribution to journalArticle

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