Tetrahedron p. 8169 - 8178 (1990)
Update date:2022-07-29
Topics:
Epifani, Erbana
Florio, Saverio
Fava, Giovanna Gasparri
2-Benzothiazolylalkyllithiums 1a-e react with epoxides 2a-d furnishing γ-hydroxyalkylbenzothiazoles 3 and 4, 5 and 6, 7 and 8, 9.The reaction of 1b with 2a and 2b proceeds with a pronounced syn-diastereoselection giving 3 and 4 (3/4 ratio > 95/5) and 5 and 6 (5/6 ratio : 86/14) respectively.Such a syn diastereoselection is rationalized in terms of transition state energy.A poor regio- and diastereoselection is observed in the reaction of 1b with 2c which leads to 7 and 8.The reaction of 1d with 2a is complicated by the selfcondensation of 1d giving a mixture of 10 and 11.
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Doi:10.1021/jo400613z
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