Tetrahedron

TiCl 4-activated selective nucleophilic substitutions of tert-butyl alcohol and benzyl alcohols with π-donating substituents

CY Tsai, R Sung, BR Zhuang, K Sung

Index: Tsai, Chen-Yu; Sung, Robert; Zhuang, Bo-Ren; Sung, Kuangsen Tetrahedron, 2010 , vol. 66, # 34 p. 6869 - 6872

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Citation Number: 11

Abstract

Ti(IV) as a Lewis acid facilitates a variety of reactions by activating various functional groups, such as aldehydes, 1, 1a and 1b carboxylates, 2, 2a, 2b, 2c, 2d and 2e acetals, 3, 3a, 3b, 3c, 3d, 3e and 3f sulfonates, 4 epoxides, 5, 5a and 5b and so on. Ti(IV) in the activation of aldehydes, carboxylates, or sulfonates significantly polarizes carbonyl or sulfonyl π bond, resulting in more electrophilic carbonyl carbon or sulfonyl sulfur, which is susceptible to various ...

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