Furan-, Pyrrole-, and Thiophene-Based Siloxydienes for Syntheses of Densely Functionalized Homochiral Compounds

Giovanni Casiraghi; Gloria Rassu

doi:10.1055/s-1995-3983

Synthesis 1995; 1995(6): 607-626
DOI: 10.1055/s-1995-3983

review

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Furan-, Pyrrole-, and Thiophene-Based Siloxydienes for Syntheses of Densely Functionalized Homochiral Compounds

Giovanni Casiraghi^* , Gloria Rassu

^*Dipartimento Farmaceutico, Università di Parma, I-43100 Parma, Italy, Fax +39(521)905006; E-mail: casirag@ipruniv.cce.unipr.it

Abstract

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This review describes the methods of preparation and use of 2-(trimethylsiloxy)furan, N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole, and certain substituted analogues and congeners, including novel 2-(tert-butyldimethylsiloxy)thiophene, to synthesize complex carbohydrates, azasugars, polyhydroxylated alkaloids, C-glycosylated α-amino acids, amino acids bearing quaternary chiral carbon atoms, and thiosugars. Especially emphasized is the preparation of enantiomerically pure compounds of biological interest. Some mechanistic insights are presented.

The aldol-type condensations of the title siloxydienes with chiral electrophilic reagents produce versatile templates to be exploited to synthesize a myriad of multifunctional compounds

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