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

Authors
Drew, MGB Harrison, RJ Mann, J Tench, AJ Young, RJ
Citation
Mgb. Drew et al., 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, TETRAHEDRON, 55(4), 1999, pp. 1163-1172
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
4
Year of publication
1999
Pages
1163 - 1172
Database
ISI
SICI code
0040-4020(19990122)55:4<1163:PAOMT5>2.0.ZU;2-1
Abstract
We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsil oxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-triisopropylsiloxy methyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4( S), S(S)-pyrrolidine-2-ones. Photoinduced addition of methano l to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected produ ct 4(S)-1'-[2'-hydroxy, 1'-( R)-N-boc-amino]ethyl-tetrahydrofuran-2-one via rearrangement of the initial photoadduct. (C) 1999 Elsevier Science Ltd. A ll rights reserved.