Double stereodifferentiation in aldol reactions on protected pyroglutamateesters

Citation
Pb. Hitchcock et al., Double stereodifferentiation in aldol reactions on protected pyroglutamateesters, TETRAHEDR L, 42(12), 2001, pp. 2381-2384
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
12
Year of publication
2001
Pages
2381 - 2384
Database
ISI
SICI code
0040-4039(20010318)42:12<2381:DSIARO>2.0.ZU;2-O
Abstract
Excellent stereoselectivity is observed at both chiral centres created in t he aldol condensation of the matched pairs of (2S)-pyroglutamate ester uret hane 1 and either (R)-glyceraldehyde acetonide 2 or the (S)-Garner aldehyde 6. Stereoselectivity was not so impressive with the mismatched pairs 1+4 o r 1+8 or when the C-2 reduced bromide 12 was used in the corresponding reac tion with aldehyde 2. (C) 2001 Elsevier Science Ltd. All rights reserved.