Three component synthesis of homoallylic amines. Efficient catalysis by lanthanum triflate/benzoic acid

Aspinall, Helen C.; Bissett, James S.; Greeves, Nick; Levin, Daniel

doi:10.1016/s0040-4039(01)02116-5

Cited by 70 publications

(17 citation statements)

References 9 publications

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“…The organic phases were combined and dried over Na 2 SO 4 . After removal of the volatile materials under reduced pressure, the residue was purified by thin-layer chromatography (AcOEt:hexane ¼ 1 : 3), affording N-(1-phenylbut-3-enyl)-panisidine; [31] yield: 60.8 mg (80%).…”

Section: Experimental Procedures Of Table 1 Entrymentioning

confidence: 99%

The Direct, Enantioselective, One‐Pot, Three‐Component, Cross‐Mannich Reaction of Aldehydes: The Reason for the Higher Reactivity of Aldimine versus Aldehyde in Proline‐Mediated Mannich and Aldol Reactions

et al. 2005

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In the proline-mediated Mannich and aldol reactions of propanal as a nucleophile, the aldimine prepared from benzaldehyde and p-anisidine is about 7 times more reactive than the corresponding aldehyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic nitrogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically verified.

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Section: Experimental Procedures Of Table 1 Entrymentioning

confidence: 99%

The Direct, Enantioselective, One‐Pot, Three‐Component, Cross‐Mannich Reaction of Aldehydes: The Reason for the Higher Reactivity of Aldimine versus Aldehyde in Proline‐Mediated Mannich and Aldol Reactions

et al. 2005

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“…This promising methodology, which allows a direct access to homoallylamines from carbonyl compounds, is an active field of research [51][52][53]. Greeves and co-workers reported that the unactivated lanthanum triflate -benzoic acid catalyses the in situ formation and allylation of various aldimines with allyltributyltin [52].…”

Section: Homoallylamine Synthesis By a Three-component Reactionmentioning

confidence: 99%

“…Greeves and co-workers reported that the unactivated lanthanum triflate -benzoic acid catalyses the in situ formation and allylation of various aldimines with allyltributyltin [52]. Solid-supported threecomponent reaction is an efficient tool in the synthesis of a library of homoallylic amines.…”

Section: Homoallylamine Synthesis By a Three-component Reactionmentioning

confidence: 99%

Recent advancements in the homoallylamine chemistry

Puentes

Kouznetsov

2002

Journal of Heterocyclic Chem

153

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“…[49][50][51][52] Furthermore, only the allyl group in allyltributyltin is delivered into the product molecule and the SnBu 3 group is usually discarded as waste after the reaction. Moreover, Lewis acids or Brønsted acids are often needed in the allylation of imines with allyltributyltin to activate the substrates, [52][53][54][55][56][57][58][59][60][61] generally because of the lower reactivity of imine compared with the corresponding aldehyde. Moreover, Lewis acids or Brønsted acids are often needed in the allylation of imines with allyltributyltin to activate the substrates, [52][53][54][55][56][57][58][59][60][61] generally because of the lower reactivity of imine compared with the corresponding aldehyde.…”

Section: Introductionmentioning

confidence: 99%