Control of Activation Mode To Achieve Diastereodivergence in Asymmetric Syntheses of Chiral Spiropiperidinone Derivatives.
J Org Chem
; 82(1): 397-406, 2017 01 06.
Article
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| MEDLINE
| ID: mdl-27936322
ABSTRACT
An efficient organocatalytic cascade reaction has been developed involving a Michael-hemiaminalization relay for the asymmetric synthesis of spiropiperidinone derivatives bearing adjacent quaternary and tertiary chiral centers via LUMO or HOMO activation. Importantly, this methodology demonstrates that applying distinct activation modes to different substrates in the same reaction can diverge diastereoselectivity. To our knowledge, this is also one of the few published cases of primary amine catalytic [3 + 3] cycloaddition reactions involving α-branched ß-ketoamides.
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01-internacional
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MEDLINE
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En
Revista:
J Org Chem
Año:
2017
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Article