Reactions between (E/Z)-Bu3SnCH2CHCHCH3 and RCHO (R  CH3, C2H5, n-C3H7, n-C4H9, n-C5H11, (CH3)2CH, (CH3)3C, C6H5, CH2CH, CH2C(CH3), (E)-CH3CHCH, (E)-C3H7CHCH, (E)-C6H5CHCH) have been carried out in the presence of Lewis acids such as Bu2SnCl2, BF3·Et2O and TiCl4. The stereochemical course of the reactions to give homoallylic alcohols does not necessarily depend on the formation of intermediate Lewis acid-aldehyde complexes, but rather upon the formation of allylmetal compounds (e.g., Bu2ClSnCH2CHCHCH3, Bu2ClSnCH(CH3)CHCH2, Cl3TiCH2CHCHCH3, etc.) which are the actual species which react with the carbonyl compounds. Bu3SnCH2CHCHCH3 does not undergo the reaction.

ALLYLSTANNATION .10. STEREOCHEMICAL COURSE OF THE ADDITION-REACTIONS OF (E/Z)-BU3SNCH2CH=CHCH3 WITH ALDEHYDES IN THE PRESENCE OF LEWIS-ACIDS (BU2SNCL2, BF3.ET2O, AND TICL4)

MARTON, DANIELE;TAGLIAVINI, GIUSEPPE;
1987

Abstract

Reactions between (E/Z)-Bu3SnCH2CHCHCH3 and RCHO (R  CH3, C2H5, n-C3H7, n-C4H9, n-C5H11, (CH3)2CH, (CH3)3C, C6H5, CH2CH, CH2C(CH3), (E)-CH3CHCH, (E)-C3H7CHCH, (E)-C6H5CHCH) have been carried out in the presence of Lewis acids such as Bu2SnCl2, BF3·Et2O and TiCl4. The stereochemical course of the reactions to give homoallylic alcohols does not necessarily depend on the formation of intermediate Lewis acid-aldehyde complexes, but rather upon the formation of allylmetal compounds (e.g., Bu2ClSnCH2CHCHCH3, Bu2ClSnCH(CH3)CHCH2, Cl3TiCH2CHCHCH3, etc.) which are the actual species which react with the carbonyl compounds. Bu3SnCH2CHCHCH3 does not undergo the reaction.
File in questo prodotto:
Non ci sono file associati a questo prodotto.
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11577/2489655
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 47
  • ???jsp.display-item.citation.isi??? 49
social impact