Three‐Component Domino Knoevenagel/Hetero‐Diels–Alder Reaction for the Synthesis of the Amino Sugars 2‐Acetoxyforosamine and 2‐Acetoxyossamine – Experimental and Theoretical Results | Zendy

Tietze Lutz F. | Zendy; Dietz Simone | Zendy; Böhnke Niels | Zendy; Düfert M. Alexander | Zendy; Objartel Ina | Zendy; Stalke Dietmar | Zendy

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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 .

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