Regioselective and diastereoselective phosphine-catalysed [3+2] cycloadditions to 5-methylenehydantoins: reversal of regioselectivity using chiral N-2-butynoyl-(4S)-benzyloxazolidinone

✍ Scribed by Tien Q Pham; Stephen G Pyne; Brian W Skelton; Allan H White

• Book ID: 104251627
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 77 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01245-5

✦ Synopsis

The phosphine-catalysed [3+2] cycloaddition of 5-methylenehydantoins 1 with the ylides 2a and 2b gives spirocyclic products with reverse regioselectivities; the latter ylide gives optically active products.