- Palladium-catalyzed preparation of Weinreb amides from boronic acids and N-methyl-N-methoxycarbamoyl chloride
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(Chemical Equation Presented) A simple protocol for the synthesis of Weinreb benzamides and α,β-unsaturated Weinreb amides through a palladium-catalyzed cross-coupling reaction between organoboronic acids and N-methoxy-N-methylcarbamoyl chloride has been developed. The method is also applicable to the use of potassium organotrifluoroborates. 2010 American Chemical Society.
- Krishnamoorthy, Ravi,Lam, Sang Q.,Manley, Christopher M.,Herr, R. Jason
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supporting information; experimental part
p. 1251 - 1258
(2010/04/29)
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- New reagent for convenient access to the α,β-unsaturated N-methoxy-N-methyl-amide functionality by a synthesis based on the Julia olefination protocol
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A new reagent for the synthesis of the α,β-unsaturated N-methoxy-N-methyl-amide structural unit has been developed. 2-(Benzo[d]thiazol-2-ylsulfonyl)-N-methoxy-N-methylacetamide, a crystalline solid with an indefinite shelf life that can be easily prepared in two convenient steps from 2-chloro-N-methoxy-N-methylacetamide, reacted with a variety of aldehydes under Julia conditions to furnish the α,β- unsaturated N-methoxy-N-methyl-amide functionality. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Manjunath, Beedimane Narayana,Sane, Neeraj P.,Aidhen, Indrapal Singh
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p. 2851 - 2855
(2007/10/03)
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- Rhodium/diene-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides
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Rhodium/chiral diene (S,S)-3b complex has been found to effectively catalyze the 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides, furnishing useful β-chiral Weinreb amides in high enantioselectivity. The Royal Society of Chemistry 2005.
- Shintani, Ryo,Kimura, Takahiro,Hayashi, Tamio
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p. 3213 - 3214
(2007/10/03)
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- Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis
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Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic β-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin.
- Chippindale, Ann M.,Davies, Stephen G.,Iwamoto, Keiji,Parkin, Richard M.,Smethurst, Christian A. P.,Smith, Andrew D.,Rodriguez-Solla, Humberto
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p. 3253 - 3265
(2007/10/03)
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