Beilstein J. Org. Chem.2007,3, No. 41, doi:10.1186/1860-5397-3-41
of enantiomeric malimide-based synthetic methodologies, [35][36][37][38] we now report concise and highly diastereoselective syntheses of an aza-spiropyran derivative 7 and (1S,8aR)-1-hydroxyindolizidine (ent-3).
Results and discussion
Previously, we have shown that the addition of Grignardreagents
PDF
Graphical Abstract
Scheme 1:
The skeletons of useful aza-spiroketals and some naturally occurring hydroxylated indolizidines.
Beilstein J. Org. Chem.2007,3, No. 8, doi:10.1186/1860-5397-3-8
phosphites have been reported using Grignardreagents [14]. In addition, 31P NMR studies showed that the addition of 1 equivalent of nBuLi to P(OPri)3 gave a mixture of P(OPri)3 and PBun3 after 15 minutes (See Supporting Information File 1 for details). Interestingly however, we have found PBun3 to be
PDF
Graphical Abstract
Scheme 1:
[3 + 3] Annelation approach to indolizidine skeleta.