A free radical method for reduction of cyclohexanones - Preferential formation of equatorial alcohols

Synthetic Communications

Volumn 33, Issue 11, 2003, Pages 1951-1961

  Clive, Derrick L J ^a   Cheng, Hua ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Alcohols; Equatorial; Ketone; Radical; Reduction; Stannanes

Indexed keywords

2 HYDROSELENOBENZOIC ACID; ALCOHOL DERIVATIVE; BENZOIC ACID DERIVATIVE; CYCLOHEXANOL DERIVATIVE; CYCLOHEXANONE DERIVATIVE; SELENIUM; SPIRO(4H 3,1 BENZOXASELENIN 2,1' CYCLOHEXAN) 4 ONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYDROLYSIS; ISOMER; REACTION OPTIMIZATION; REDUCTION; TEMPERATURE DEPENDENCE;

EID: 0038583523     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120020210     Document Type: Article

References (13)

1. 2 reagent for generating an equatorial alcohol. J. Org. Chem. 1999, 64, 4397-4410.
2. (a) Yadav, V.K.; Fallis, A. Cyclopentane synthesis and annulation: intramolecular radical cyclization of acetals. Tetrahedron Lett. 1988, 29, 897-890;
3. (b) Yadav, V.K.; Fallis, A. Cyclopentane synthesis and annulation II: radical cyclizations of oxathiolanones. Tetrahedron Lett. 1989, 30, 3283-3286;
4. (c) Yadav, V.K.; Fallis, A. Free-radical based cycloalkanol synthesis and annulation from thioacetal precursors. Can. J. Chem. 1991, 69, 779-789.
5. Cf. (a) Damm, W.; Giese, B.; Hartung, J.; Hasskerl, T.; Houk, K.N.; Hüter, O.; Zipse, H. Diastereofacial selectivity in reactions of substituted cyclohexyl radicals. An experimental and theoretical study. J. Am. Chem. Soc. 1992, 114, 4067-4079;
6. 2. Tetrahedron Lett. 2002, 43, 1701-1703.
7. Made (57%) from thiobenzilic acid and 4-(1,1-dimethylethyl)cyclohexanone, according to a general procedure: Swansburg, S.; Janz, K.; Jocys, G.; Pincock, A.; Pincock. Facial selectivity in the addition of nucleophiles to radical cations of substituted 2-methyleneadamantanes. J. Can. J. Chem. 1998, 76, 35-47.
8. Made (57%) by heating thiobenzilic acid with 4-(1,1-dimethylethyl)cyclohexanone in PhH, using a Dean-Stark apparatus.
9. Kamiyama, T.; Enomoto, S.; Inoue, M. Synthesis of mercaptobenzoic acids and mercaptopyridines using elemental sulfur in the presence of NaOH-KOH. Chem. Pharm. Bull. 1985, 33, 5184-5189.
10. Schoeller, A. Über eine enfache und bequeme methode zur darstellung aromatischer selenverbindungen. Ber. 1919, 52, 1517-1518.
11. Clive, D.L.J.; Wickens, P.L.; Sgarbi, P.W.M. Synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides by reaction of 5′-protected nucleoside 2′-3′-dimesylates with telluride dianion: a general route from cis vicinal diols to olefins. J. Org. Chem. 1996, 61, 7426-7437.
12. Lesser, R.; Weiss, R. Über den "selen-indigo" (bis-selenonaphthen-indigo) und selenhaltige aromatische verbindungen. Ber. 1912, 45, 1835-1841.
13. Shiner, V.J., Jr.; Ensinger, M.W. γ-Silicon Stabilization of Carbonium Ions in Solvolysis. 4. Solvolysis of cis- and trans-3-(Trimethylsilyl)cyclohexyl and 3-tert-Butycyclohexyl p-Bromobenzenesulfonates. J. Org. Chem. 1990, 55, 653-661.