Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins.

Journal article

The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials.

Authors: Davies, S; Fletcher, A; Lee, J; Roberts, P; Souleymanou, M

• Publication status: Published
• Journal: Organic and biomolecular chemistry
• Volume: 12
• Issue: 17
• Pages: 2702-2728
• Publication date: 2014-05-01
• DOI: 10.1039/c4ob00274a
• EISSN: 1477-0539
• ISSN: 1477-0520
• Language: English