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ChemInform Abstract: Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes: Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones.

✍ Scribed by J. BARLUENGA; F. AZNAR; C. RIBAS; C. VALDES

Publisher
John Wiley and Sons
Year
2010
Weight
37 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Cycloaddition

Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes:

Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones.

-Reaction of enantiomerically pure (E)-dienes (I) with nitroalkenes followed by hydrolysis of the resulting enamine furnishes the title compounds diastereoselectively (except (IIIf)) and with good to moderate enantioselectivity. (Z)-diene (VI) furnishes open-chain products or the corresponding furan derivatives. Investigation of the solvent influence indicates a stepwise reaction pathway via Michael type 1,4-addition and intramolecular

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