Study of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky's diene

Discovery of New Multi Component Reactions with Combinatorial Methods

“…For the described strategy and using a program based on the Daylight reaction toolkit program suite 15 such a newly proposed reaction is given in Scheme 5. This recently reported hetero Diels-Alder reaction 16 is catalysed by Lewis acids and may work also when performed as a 3CR.…”

Imino‐Diels–Alder Reactions of 1‐Aryl‐3‐(trialkylsiloxy)‐1,3‐butadienes in Solution and the Solid Phase

“…The residue was dissolved in CH 2 Cl 2 and washed with aqueous saturated NaHCO 3 solution. The organic layer was dried with Na 2 SO 4 , and the solvents were evaporated. The residue was purified by col- Imino-Diels-Alder Reaction and Deprotection: ZnCl 2 (10 %) was mixed with the chiral imine 8 (1 equiv.)…”

“…[3] The asymmetric azaDiels-Alder reaction of Danishefsky's diene with imines has also been performed by a number of different approaches, for example, with chiral imines, [4] chiral catalysts, [5] or chiral ionic liquids [6] as the chiral medium, to produce 2,3-dihydro-4-pyridones with regio-, diastereo-, and enantioselective control. The reaction has also been studied from a theoretical viewpoint.…”

Stereoselective Synthesis of Chiral 2,3‐Disubstituted 2,3‐Dihydro‐4(1H)‐pyridones

“…[3] As a part of a programme aimed at the design and preparation of polyfunctionalised, chiral building blocks that are useful for the asymmetric synthesis of biologically active nitrogen-containing compounds, we have studied the behaviour of (R)-2-[(S)-1,2-bis(benzyloxy)ethyl]-1-[(S)-1-phenylethyl]-2,3-dihydro-4(1H)-pyridone (1) as a synthetic precursor to obtain chiral 2,3-disubstituted 2,3-dihydro-4(1H)-pyridones in enantiomerically pure form. This synthetic intermediate is easily available on gram scale from inexpensive -mannitol, [4] which comes from renewable sources. The ease with which C-2 and/or C-4 can be functionalised is well illustrated by the expedient asymmetric synthesis of (R)-4-oxopipecolic acid, [5] (2S,4R)-1-(tert-butoxycarbonyl)-N-tert-butyl-4-hydroxypipecolamide, [6] (R)-and (S)-2-substituted 4-alkylidenepiperidines, [7] (2R,4S)-and (2R,4R)-4-phosphonomethylpiperidine-2-carboxylic acids, [8] cis-and trans-1,2,4-trisubstituted piperidines, [9] (R)-quinuclidine-2-carboxylic acid [10] and (2R,4R)-N-(tert-butoxycarbonyl)-4-[2-(methoxycarbonylamino)ethyl]pipecolic acid.…”

“…This synthetic intermediate is easily available on gram scale from inexpensive -mannitol, [4] which comes from renewable sources. The ease with which C-2 and/or C-4 can be functionalised is well illustrated by the expedient asymmetric synthesis of (R)-4-oxopipecolic acid, [5] (2S,4R)-1-(tert-butoxycarbonyl)-N-tert-butyl-4-hydroxypipecolamide, [6] (R)-and (S)-2-substituted 4-alkylidenepiperidines, [7] (2R,4S)-and (2R,4R)-4-phosphonomethylpiperidine-2-carboxylic acids, [8] cis-and trans-1,2,4-trisubstituted piperidines, [9] (R)-quinuclidine-2-carboxylic acid [10] and (2R,4R)-N-(tert-butoxycarbonyl)-4-[2-(methoxycarbonylamino)ethyl]pipecolic acid. [11] [a] Departamento de Química Orgánica, Instituto In this paper, we detail the functionalisation of 2,3-dihydro-4(1H)-pyridone 1 at C-3 with the diastereoselective alkylation of the corresponding enolate as a synthetic strategy.…”