Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

✍ Scribed by Michael G.B. Drew; R.John Harrison; John Mann; Allen J. Tench; Robert J. Young

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 513 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)01094-1

✦ Synopsis

We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyi--N-boc-dihydropyrrole-2(SH)-one to produce 5(S)-5-triisopropylsiloxymethyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4(S), 5(S)-pyrrolidine-2-ones. Photoinduced addition of methanol to 5( R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-l'-[2'-hydroxy, 1 '-( R)-N-boc-amino]ethyl-tetrabydrofilran-2-one via rearrangement of the initial photoadduct.