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Highly stereoselective construction of spiro[4.5]decanes by SmI(2)-promoted ketyl radical mediated tandem cyclization.
Org Lett. 2007 Feb 01; 9(3):469-72.OL

Abstract

[reaction: see text] Ketyl radical mediated tandem cyclization of omega-alkynyl carbonyl compounds bearing activated alkene using SmI(2) gave spiro[4.5]decanes stereoselectively. In the presence of HMPA, alpha,beta-unsaturated esters and alkenyl phosphonates were converted to spiro[4.5]decanes and a monocyclic compound, respectively. In the presence of Sm, bicyclic lactones were obtained from alpha,beta-unsaturated esters. The spiro[4.5]decane was provided from an alkenyl phosphonate. Interestingly, the stereochemical changeover at the first cyclization has been controlled by means of a variety of activators.

Authors+Show Affiliations

Inui M
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Nakazaki A
No affiliation info available
Kobayashi S
No affiliation info available

MeSH

AlkanesAlkenesAlkynesBridged Bicyclo CompoundsCyclizationEstersFree RadicalsLactonesModels, ChemicalOrganophosphonatesSpiro CompoundsStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17249789

Citation

Inui, Masaharu, et al. "Highly Stereoselective Construction of Spiro[4.5]decanes By SmI(2)-promoted Ketyl Radical Mediated Tandem Cyclization." Organic Letters, vol. 9, no. 3, 2007, pp. 469-72.
Inui M, Nakazaki A, Kobayashi S. Highly stereoselective construction of spiro[4.5]decanes by SmI(2)-promoted ketyl radical mediated tandem cyclization. Org Lett. 2007;9(3):469-72.
Inui, M., Nakazaki, A., & Kobayashi, S. (2007). Highly stereoselective construction of spiro[4.5]decanes by SmI(2)-promoted ketyl radical mediated tandem cyclization. Organic Letters, 9(3), 469-72.
Inui M, Nakazaki A, Kobayashi S. Highly Stereoselective Construction of Spiro[4.5]decanes By SmI(2)-promoted Ketyl Radical Mediated Tandem Cyclization. Org Lett. 2007 Feb 1;9(3):469-72. PubMed PMID: 17249789.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Highly stereoselective construction of spiro[4.5]decanes by SmI(2)-promoted ketyl radical mediated tandem cyclization. AU - Inui,Masaharu, AU - Nakazaki,Atsuo, AU - Kobayashi,Susumu, PY - 2007/1/26/pubmed PY - 2007/4/10/medline PY - 2007/1/26/entrez SP - 469 EP - 72 JF - Organic letters JO - Org Lett VL - 9 IS - 3 N2 - [reaction: see text] Ketyl radical mediated tandem cyclization of omega-alkynyl carbonyl compounds bearing activated alkene using SmI(2) gave spiro[4.5]decanes stereoselectively. In the presence of HMPA, alpha,beta-unsaturated esters and alkenyl phosphonates were converted to spiro[4.5]decanes and a monocyclic compound, respectively. In the presence of Sm, bicyclic lactones were obtained from alpha,beta-unsaturated esters. The spiro[4.5]decane was provided from an alkenyl phosphonate. Interestingly, the stereochemical changeover at the first cyclization has been controlled by means of a variety of activators. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17249789/Highly_stereoselective_construction_of_spiro[4_5]decanes_by_SmI_2__promoted_ketyl_radical_mediated_tandem_cyclization_ L2 - https://doi.org/10.1021/ol0628255 DB - PRIME DP - Unbound Medicine ER -