Tags

Type your tag names separated by a space and hit enter

Ruthenium-catalyzed diyne hydrative cyclization: synthesis of substituted 1,3-diene synthons.
Org Lett. 2005 May 26; 7(11):2097-9.OL

Abstract

[reaction: see text]. A novel and versatile strategy for the synthesis of highly functionalized substituted 3-sulfolenes based on [CpRu(CH3CN)3]PF6-catalyzed hydrative cyclization has been developed. A marked ketone directing effect in ruthenium-catalyzed cyclization was observed for the first time. This provides complementary chemoselectivity for the synthesis of 3-sulfolenes and other cyclic enones. The utility of this method has been demonstrated by SO2 extrusion of 3-sulfolenes to afford 1,3-dienes and the subsequent inter- and intramolecular Diels-Alder reaction.

Authors+Show Affiliations

Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.eduNo affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15901143

Citation

Trost, Barry M., and Xiaojun Huang. "Ruthenium-catalyzed Diyne Hydrative Cyclization: Synthesis of Substituted 1,3-diene Synthons." Organic Letters, vol. 7, no. 11, 2005, pp. 2097-9.
Trost BM, Huang X. Ruthenium-catalyzed diyne hydrative cyclization: synthesis of substituted 1,3-diene synthons. Org Lett. 2005;7(11):2097-9.
Trost, B. M., & Huang, X. (2005). Ruthenium-catalyzed diyne hydrative cyclization: synthesis of substituted 1,3-diene synthons. Organic Letters, 7(11), 2097-9.
Trost BM, Huang X. Ruthenium-catalyzed Diyne Hydrative Cyclization: Synthesis of Substituted 1,3-diene Synthons. Org Lett. 2005 May 26;7(11):2097-9. PubMed PMID: 15901143.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium-catalyzed diyne hydrative cyclization: synthesis of substituted 1,3-diene synthons. AU - Trost,Barry M, AU - Huang,Xiaojun, PY - 2005/5/20/pubmed PY - 2006/2/28/medline PY - 2005/5/20/entrez SP - 2097 EP - 9 JF - Organic letters JO - Org Lett VL - 7 IS - 11 N2 - [reaction: see text]. A novel and versatile strategy for the synthesis of highly functionalized substituted 3-sulfolenes based on [CpRu(CH3CN)3]PF6-catalyzed hydrative cyclization has been developed. A marked ketone directing effect in ruthenium-catalyzed cyclization was observed for the first time. This provides complementary chemoselectivity for the synthesis of 3-sulfolenes and other cyclic enones. The utility of this method has been demonstrated by SO2 extrusion of 3-sulfolenes to afford 1,3-dienes and the subsequent inter- and intramolecular Diels-Alder reaction. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15901143/Ruthenium_catalyzed_diyne_hydrative_cyclization:_synthesis_of_substituted_13_diene_synthons_ DB - PRIME DP - Unbound Medicine ER -