Facile synthesis and unusual methanesulfonylation reaction of (2R,3R)-1,4-dimethoxy-1,1,4,4-tetrasubstituted-2,3-butanediols

Synthetic Communications

Volumn 37, Issue 15, 2007, Pages 2483-2490

  Srimurugan, Sankareswaran ^a   Suresh, Paulsamy ^a   Viswanathan, Balasubramanian ^a   Varadarajan, Thirukkallam Kanthadai ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Chiral diols; Cyclic sulfate; Hydroxybenzoate esters; Oxidative cleavage; Steric hindrance

Indexed keywords

BUTANEDIOL; SULFITE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; OXIDATION KINETICS; SULFONATION; SYNTHESIS;

EID: 34547871297     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701462153     Document Type: Article

References (13)

1. Cremlyn, R. An Introduction to Organosulfur Chemistry; John Wiley & Sons: Chichester, 1996, chap. 7, pp. 93-120.
2. Srikrishna, A.; Gharpure, S. J. Novel formation of cloromethanesulfinates in the mthanesulfonylation reaction of hindered alcohols. Synlett 2000, 9, 1354-1356.
3. Zhang, M.; Yin, D. A.; Guo, J. Y.; Liang, X. T. An unusual formation of cyclic sulfite at C-4 and C-5 positions of taxane. Chin. Chem. Lett. 2004, 15, 1033-1055.
4. (a) Srimurugan, S.; Viswanathan, B.; Varadarajan, T. K.; Varghese, B. Microwave-assisted cyclocondensation of dialdehydes with chiral diamines forming calixsalen-type macrocycles. Tetrahedron Lett. 2005, 46, 3151-3155;
5. (b) Srimurugan, S.; Viswanathan, B.; Varadarajan, T. K.; Varghese, B. Synthesis and crystal structure of [2 + 2] calixsalens. Org. Bimol. Chem. 2006, 3044-3047.
6. Mash, E. A.; Hemperly, S. B.; Nelson, K. A.; Heidt, P. C.; Van Deusen, S. Mechanistic studies of diastereoselective cyclopropanation via homochiral ketals, 1: Dioxolane structural effects. J. Org. Chem. 1990, 55, 2045-2055.
7. Mears, R. J.; Sailes, H. E.; Watts, J. P.; Whiting, A. Synthesis, structure and comparative stability of β-hydrazono, oximino methyl ether and imino boronates. J. Chem. Soc., Perkin Trans. 1 2000, 3250-3263.
8. (a) Wunsch, B.; Nerdinger, S. Diastereoselective addition of chiral (2-lithiophenyl) acetaldehyde acetals to various imines as key step in the asymmetric synthesis of 1-aryltetrahydroisoquinolines, Part 4. Eur. J. Org. Chem. 1999, 503-517;
9. (b) Luithle, J. E. A.; Pietruszka, J. Synthesis of enantiomerically pure cyclopropanes from cyclopropylboronic acids. J. Org. Chem. 1999, 64, 8287-8297.
10. Conole, G.; Mears, R. J.; De Silva, H.; Whiting, A. The mechanism of directed remote asymmetric reduction of carbonyl groups via homochiral boronate esters. J. Chem. Soc., Perkin Trans. 1 1995, 1825-1836.
11. 4 reagent under two-phase conditions. Tetrahedron Lett. 1999, 40, 8439-8441.
12. Gao, Y.; Sharpless, K. B. Vicinal diol cyclic sulfates: Like epoxides only more reactive. J. Am. Chem. Soc. 1988, 110, 7538-7539.
13. Van Woerden, H. F. Organic sulfites. Chem. Rev. 1963, 63, 557-571.