754989-19-0Relevant academic research and scientific papers
Stereoselective β-hydroxy-α-amino acid synthesis via an ether-directed, palladium-catalysed aza-Claisen rearrangement
Fanning, Kate N.,Jamieson, Andrew G.,Sutherland, Andrew
, p. 3749 - 3756 (2005)
A highly diastereoselective synthesis of (2S,3S)-β-hydroxy-α- amino acids has been developed from enantiopure α-hydroxy acids using a MOM-ether-directed, palladium(II)-catalysed, aza-Claisen rearrangement of allylic acetimidates to effect the key step. This highly stereoselective process gave allylic amides in diastereomeric ratios of up to 14 : 1. Problems associated with the isolation of 1,3-products (anti-Claisen) from sterically demanding substrates via an in situ palladium(0)-catalysed rearrangement process were overcome by the addition of a re-oxidant, p-benzoquinone, leading to cleaner reactions and improved yields of the 3,3-products (Claisen). The target β-hydroxy-α-amino acids are an important class of natural products that are also components of more complex organic compounds with significant biological properties. The Royal Society of Chemistry 2005.
A new general approach for the stereocontrolled synthesis of functionalised γ- And δ-lactams
Daly, Mark,Gill, Kathryn,Sime, Mairi,Simpson, Graham L.,Sutherland, Andrew
experimental part, p. 6761 - 6770 (2011/11/06)
A new flexible approach for the stereoselective synthesis of substituted 1H-pyrrol-2(5H)-ones and 3,6-dihydro-1H-pyridin-2-ones has been developed. The general strategy employed the stereoselective reduction of a series of α,β-unsaturated ketones under ch
Simple deprotection of acetal type protecting groups under neutral conditions
Miyake, Hideyoshi,Tsumura, Takatsugu,Sasaki, Mitsuru
, p. 7213 - 7215 (2007/10/03)
Heating acetals with ethylene glycol causes the deprotection of acetal type protecting groups. When acetals such as MOM ethers, MEM ethers, and THP ethers were heated in ethylene glycol or propylene glycol, solvolysis proceeded smoothly to produce alcohols in excellent yield. This reaction is a very promising method for chemoselective deprotection of acetal type protecting groups.
