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Three‐Component Domino Knoevenagel/Hetero‐Diels–Alder Reaction for the Synthesis of the Amino Sugars 2‐Acetoxyforosamine and 2‐Acetoxyossamine – Experimental and Theoretical Results
Author(s) -
Tietze Lutz F.,
Dietz Simone,
Böhnke Niels,
Düfert M. Alexander,
Objartel Ina,
Stalke Dietmar
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100725
Subject(s) - chemistry , knoevenagel condensation , domino , reductive amination , diels–alder reaction , nitro , organic chemistry , formaldehyde , amination , catalysis , alkyl
The three‐component domino Knoevenagel/hetero‐Diels–Alder reaction of nitroacetone ( 6 ), formaldehyde and ethoxyvinylacetate ( 4 ) leads to dihydropyrans 10 and 11 , which after hydrogenation of the double bond as well as consecutive reduction of the nitro group and reductive amination give the desired forosamine‐type 2‐acetoxyamino sugars 21 – 24 and ossamine‐type 25 .