Allylstannanes and vinylstannanes from stannylcupration of C-C multiple bonds. Recent advances and applications in organic synthesis.
The stannylcupration of allenes and alkynes has emerged as a powerful tool for the synthesis of allyl- and vinylorganostannanes. The regio- and stereoselectivity of this reaction depends upon the nature of the cuprate, the temperature and the structure of the allene or alkyne. The versatility and synthetic scope of the tin-synthons thus obtained is very wide. These intermediates have been employed as precursors in the key step of the stereoselective synthesis of many natural products, heterocycles or conjugated polyenes. This tutorial review shows a general survey of the recent advances in this area together with the contribution of our lab to this field.
Barbero
Asunción
A
Departamento de Química Orgánica, Facultad de Ciencias, c/Dr Mergelina s/n, 47011 Valladolid, Spain. barbero@qo.uva.es
Pulido
Francisco J
FJ
D000466:Alkadienes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000498:Allyl Compounds / Q000138:chemical synthesis*; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009947:Organotin Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D000466:Alkadienes; D000480:Alkynes; D000498:Allyl Compounds; D009947:Organotin Compounds; D014753:Vinyl Compounds; C025947:propadiene; D003300:Copper