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Highly Stereoselective and Efficient Addition of Organocerium Reagents to syn-β-Alkyl-β-hydroxy-α-methyl Ketones by Way of Their Titanium Alkoxides − Synthesis of Complex 1,3-Diol Units with Three Stereodefined Centres

✍ Scribed by Giuseppe Bartoli; Marcella Bosco; Emanuela Di Martino; Enrico Marcantoni; Letizia Sambri


Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
342 KB
Volume
2001
Category
Article
ISSN
1434-193X

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✦ Synopsis


A highly efficient and stereoselective technique for additions to syn-β-alkyl-β-hydroxy-α-methyl ketones is now available. The methodology is based on the conversion of the starting material into a trichlorotitanium alkoxide derivative, which is able to assume a stable cyclic arrangement exhibiting high stereofacial discrimination towards nucleophilic alkyl transfer by an appropriate organometallic species. The use of Grignard reagents has serious limitations; in fact, highly