Organic Chemistry Portal

Abstracts

Search:

Chiral Bifunctional Phosphine Ligand Enabling Gold-Catalyzed Asymmetric Isomerization of Alkyne to Allene and Asymmetric Synthesis of 2,5-Dihydrofuran

Xinpeng Cheng, Zhixun Wang, Carlos D. Quintanilla, Liming Zhang*

*Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: zhangchem.ucsb.edu

X. Cheng, Z. Wang, C. D. Quintanilla, L. Zhang, J. Am. Chem. Soc., 2019, 141, 3787-3791.

DOI: 10.1021/jacs.8b12833


see article for more reactions

Abstract

Gold catalysis using a chiral bifunctional biphenyl-2-ylphosphine ligand provides 2,5-disubstituted 2,5-dihydrofurans from chiral propargylic alcohols as substrates in typically good yields and with good to excellent diastereoselectivities. With achiral substrates, 2,5-dihydrofurans are formed with good to excellent enantiomeric excesses.

see article for more examples



Key Words

2,5-dihydrofurans


ID: J48-Y2019