497968-38-4

Upstream product

• 534-22-5 2-methylfuran 
• 139190-71-9 N-benzyl-N-benzyloxycarbonyl-L-alaninal 
• 497968-32-8 (1S,2S)-N-benzyl-N-[2-(5-methylfuran-2-yl)-2-hydroxy-1-methylethyl]carbamic acid benzyl ester 

Downstream Products

• 497968-33-9 (1S,2S)-N-benzyl-N-[2-(5-methylfuran-2-yl)-2-hydroxy-1-methylethyl]carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Asymmetric addition of 2-methylfuran and its lithiated derivative to variously N,N-protected L-alaninals

The asymmetric reaction of 2-methylfuran 2a and its lithiated derivative 2b with N,N-diprotected L-alaninals 1a-c, carried out under high pressure conditions in the presence of Lewis acid-catalyst, are described. For aldehyde 1a two diastereoisomeric adducts anti-3a and syn-3a were formed, with predominance of the former. In the case of aldehydes 1b and 1c only the anti-diastereoisomers 3b or 3c were formed, but accompanied by two diastereoisomeric oxazolidinones trans-4 and cis-4. The absolute configuration (via X-ray analysis of anti-5 and chemical correlations) and the extent of asymmetric induction were established.