HIGHLY DIASTEREOSELECTIVE, NUCLEOPHILIC ALKENOYLATION OF ENANTIOPURE ALPHA-OXY-ALKANAL AND ALPHA-AMINO-ALKANAL BY LITHIATED [1-(P-TOLNENESULFONYL)ALK-2-ENYL] CARBAMATES - REVISION OF THE STEREOCHEMISTRY AND APPLICATION TO THE SYNTHESIS OF A DIHYDROXYETHYLENE DIPEPTIDE ISOSTERE

Authors
HOPPE D TEBBEN P REGGELIN M BOLTE M
Citation
D. Hoppe et al., HIGHLY DIASTEREOSELECTIVE, NUCLEOPHILIC ALKENOYLATION OF ENANTIOPURE ALPHA-OXY-ALKANAL AND ALPHA-AMINO-ALKANAL BY LITHIATED [1-(P-TOLNENESULFONYL)ALK-2-ENYL] CARBAMATES - REVISION OF THE STEREOCHEMISTRY AND APPLICATION TO THE SYNTHESIS OF A DIHYDROXYETHYLENE DIPEPTIDE ISOSTERE, Synthesis, (2), 1997, pp. 183
Citations number
55
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
2
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):2<183:HDNAOE>2.0.ZU;2-E
Abstract
The addition of lithiated [1-(p-toluenesulfonyl)alk-2-enyl] carbamates to alpha-stereogenic aldehydes proceeds with steric approach control according to the Felkin-Anh model to produce alpha'-carbamoyloxy-alpha ,beta-enones by carbonyl migration and elimination of p-toluenesulfina te. Conversion of two enones to 1,3-dioxan-2-one 9 and to bamoyloxy)-3 -hydroxy-2-isopropyl-7-methyloctanoate (16a), respectively, furnished samples suitable for X-ray crystal structure analyses to confirm the s tereochemical course of the addition step.