Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins

Yun Yang; Shou-Fei Zhu; Chang-Yue Zhou; Qi-Lin Zhou

doi:10.1021/ja805296k

Nickel-catalyzed enantioselective alkylative coupling of alkynes and aldehydes: synthesis of chiral allylic alcohols with tetrasubstituted olefins

J Am Chem Soc. 2008 Oct 29;130(43):14052-3. doi: 10.1021/ja805296k. Epub 2008 Oct 4.

Authors

Yun Yang¹, Shou-Fei Zhu, Chang-Yue Zhou, Qi-Lin Zhou

Affiliation

¹ State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.

PMID: 18834121
DOI: 10.1021/ja805296k

Abstract

A highly efficient nickel-catalyzed asymmetric alkylative coupling of alkynes, aldehydes, and dimethylzinc has been realized by using bulky spirobiindane phosphoramidite ligands, affording allylic alcohols with a tetrasubstituted olefin functionality in high yields, high regioselectivities, and excellent enantioselectivities.

MeSH terms

Aldehydes / chemistry*
Alkenes / chemical synthesis*
Alkenes / chemistry
Alkylation
Alkynes / chemistry*
Catalysis
Ligands
Molecular Structure
Nickel / chemistry*
Organometallic Compounds / chemistry*
Organophosphorus Compounds / chemistry
Propanols / chemical synthesis*
Propanols / chemistry
Spiro Compounds / chemistry
Stereoisomerism
Zinc / chemistry

Substances

Aldehydes
Alkenes
Alkynes
Ligands
Organometallic Compounds
Organophosphorus Compounds
Propanols
Spiro Compounds
phosphoramidite
allyl alcohol
Nickel
Zinc