Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

Hsyueh-Liang Wu, Ping Yu Wu, Ying Ni Cheng, Biing Jiun Uang

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.

Original languageEnglish
Pages (from-to)2656-2665
Number of pages10
JournalTetrahedron
Volume72
Issue number21
DOIs
Publication statusPublished - 2016 May 26

Fingerprint

Camphor
Carbonyl compounds
Enantioselectivity
Sulfhydryl Compounds
Aldehydes
Carbon
Ligands
Addition reactions
Catalyst activity
Alcohols

Keywords

  • Catalytic asymmetric 1,2-addition reaction
  • Chiral alcohols
  • Chiral amino thiol ligand
  • Organozinc reagents

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand. / Wu, Hsyueh-Liang; Wu, Ping Yu; Cheng, Ying Ni; Uang, Biing Jiun.

In: Tetrahedron, Vol. 72, No. 21, 26.05.2016, p. 2656-2665.

Research output: Contribution to journalArticle

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