Enantioselective One‐Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction | Zendy

Šebesta Radovan | Zendy; Bilčík Filip | Zendy; Fodran Peter | Zendy

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Enantioselective One‐Pot Conjugate Addition of Grignard Reagents Followed by a Mannich Reaction

Author(s) -

Šebesta Radovan,

Bilčík Filip,

Fodran Peter

Publication year - 2010

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.201000773

Subject(s) - chemistry , enantioselective synthesis , stereocenter , diastereomer , conjugate , reagent , ferrocene , mannich reaction , grignard reaction , organic chemistry , grignard reagent , cyclohexenone , addition reaction , catalysis , mathematical analysis , mathematics , electrode , electrochemistry

Asymmetric addition of Grignard reagents to cyclohexenone, catalyzed by ferrocene diphosphanes, afforded chiral magnesium enolates. These enolates reacted in a one‐pot arrangement with N ‐benzylidenetoluenesulfonamide to give β‐amino carbonyl compounds with three contiguous stereocenters. Two major diastereoisomers ( dr = 60:40) of product with enantioselectivities up to 95 % ee were separated by flash chromatography.

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