Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex

Xin-Bin Yang; Jie Feng; Ji Zhang; Na Wang; Li Wang; Jun-Liang Liu; Xiao-Qi Yu

doi:10.1021/ol8001706

Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex

Org Lett. 2008 Mar 20;10(6):1299-302. doi: 10.1021/ol8001706. Epub 2008 Feb 28.

Authors

Xin-Bin Yang¹, Jie Feng, Ji Zhang, Na Wang, Li Wang, Jun-Liang Liu, Xiao-Qi Yu

Affiliation

¹ Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), and West China Hospital, West China Medical School, Sichuan University, Chengdu, Sichuan 610041, PR China.

PMID: 18303907
DOI: 10.1021/ol8001706

Abstract

3-diphenylhydroxymethyl-substituted BINOL-titanium complex prepared in situ was found to be a highly efficient catalyst for hetero-Diels-Alder reaction of diene 1 with both aromatic and aliphatic aldehydes to give 2,5-disubstituted dihydropyrone in up to 99% yield and 99% ee.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Butadienes / chemistry*
Catalysis
Molecular Structure
Naphthols / chemistry*
Stereoisomerism
Titanium / chemistry*

Substances

Aldehydes
BINOL, naphthol
Butadienes
Naphthols
Titanium