Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

Davies, Stephen G.; Durbin, Matthew J.; Hartman, Scott J.S.; Matsuno, Ai; Roberts, Paul M.; Russell, Angela J.; Smith, Andrew D.; Thomson, James E.; Toms, Steven M.

doi:10.1016/j.tetasy.2008.11.019

Cited by 32 publications

(10 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This reagent control, when combined with that of the α,β-unsaturated ester (substrate control: production of the 3,4- syn -diastereoisomer favored), results in very highly selective reactions. These results suggest that α,β-unsaturated esters (±)- 22 – 26 are viable substrates for our PKR protocol (Scheme ).…”

mentioning

confidence: 69%

“…Such is the importance of kinetic resolution that over 100 years later it, together with dynamic kinetic resolution (DKR) and parallel kinetic resolution (PKR), is employed widely in the preparation of enantiomerically pure materials on both laboratory and industrial scales. We have previously developed the PKR of a range of chiral 3- and 5-substituted cyclopent-1-enecarboxylates, and 6-substituted cyclohex-1-enecarboxylates using a 50:50 pseudoenantiomeric mixture of enantiopure lithium amides . This protocol has thus far been limited to these cyclic α,β-unsaturated esters due to the requirement for high levels of substrate control.…”

mentioning

confidence: 99%

“…When investigating PKR, we have promulgated that it is prudent to follow a strategy of first investigating the levels of substrate control offered by the chiral α,β-unsaturated ester upon conjugate addition of an achiral lithium amide, viz. lithium N -benzyl- N -isopropylamide 29 .…”

mentioning

confidence: 99%

See 2 more Smart Citations

Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

et al. 2011

Self Cite

View full text Add to dashboard Cite

Conjugate addition of a 50:50 pseudoenantiomeric mixture of lithium (R)-N-benzyl-N-(α-methylbenzyl)amide and lithium (S)-N-3,4-dimethoxybenzyl-N-(α-methylbenzyl)amide to a range of racemic acyclic γ-amino-α,β-unsaturated esters (derived from the corresponding α-amino acids) effects their efficient parallel kinetic resolution, allowing the preparation of enantiopure β,γ-diamino esters. The β,γ-diamino ester products of these reactions are readily converted into the corresponding substituted 4-aminopyrrolidin-2-ones via N-debenzylation and cyclization.

show abstract

mentioning

confidence: 69%

mentioning

confidence: 99%

See 1 more Smart Citation

Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

et al. 2011

Self Cite

View full text Add to dashboard Cite

show abstract

“…Hydrogenolysis and ester hydrolysis gave (1R,2S,5S)-and (1S,2R,5R)-5-methylcispentacin (99 and 100) in 98% ee (Figure 8; for 5-alkyl-substituted cispentacins, see also ref 19). 22 The parallel kinetic resolution strategy based on conjugate addition was efficiently used for the preparation of 6-methylsubstituted β-aminocyclohexanecarboxylic acid enantiomers 23 and 3-alkyl-substituted cispentacin enantiomers. 24 Chiral lithium amide (80) addition to unsaturated cyclic esters (79; Scheme 14) provided cis-β-amino ester 81, while the N-protected transpentacin could be easily prepared by epimerization of 81 at C-1 with base.…”

Section: Amentioning

confidence: 99%

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

View full text Add to dashboard Cite

Introduction 1116 2. Carbocyclic β-Amino Acids 1118 2.1. Syntheses of Five-or Six-Membered Carbocyclic β-Amino Acids 1118 2.1.1. Carbocyclic β-Amino Acids from β-Keto Esters 1119 2.1.2. Carbocyclic β-Amino Acids by Metathesis 1119 2.1.3. Carbocyclic β-Amino Acids by Amino Group Conjugate Addition 1122 2.1.4. Carbocyclic β-Amino Acids by Cycloaddition 1124 2.1.5. Carbocyclic β-Amino Acids by Desymmetrization of meso-Anhydrides 1124 2.1.6. Carbocyclic β-Amino Acids from Natural Sources 1125 2.1.7. Miscellaneous 1127 2.2. Syntheses of Small-Ring Carbocyclic β-Amino Acids 1128 2.3. Syntheses of Carbocyclic β-Amino Acids with Larger Ring Systems 1129 2.4. Synthesis of Functionalized Carbocyclic β-Amino Acids 1131 2.4.1. Syntheses of Functionalized Cyclic β-Amino Acids by C−C Double Bond Functionalization 1131 2.4.2. Several Relevant Routes to Functionalized Cyclic β-Amino Acids Other Than Functionalization of the Ring C−C Double Bond 1137 3. Cyclic β-Amino Acids with a Heteroatom in the Ring 1137 3.1. Syntheses of Cyclic β-Amino Acids with a N Atom in the Ring 1138 3.1.1. Three-and Four-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.2. Five-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.3. Six-Membered N-Containing Cyclic β-Amino Acids 1145 3.1.4. N-Containing Cyclic β-Amino Acids with Larger Ring Systems 1148 3.2. Syntheses of Cyclic β-Amino Acids with an O Atom in the Ring 1148 3.2.1. Four-Membered O-Containing Cyclic β-Amino Acids 1148 3.2.2. Five-Membered O-Containing Cyclic β-Amino Acids 1149 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids 1155 3.3. Cyclic β-Amino Acids with Other Heteroatoms in the Ring 1159 4. Some Relevant Biological Properties of Cyclic β-Amino Acids 1160 4.1. Cyclic β-Amino Acids Possessing Antifungal or Antibacterial Properties 1160 4.2. Antiviral Cyclic β-Amino Acids 1162 4.3. Cyclic β-Amino Acids with Antitumoral Properties 1162 4.4. Cyclic β-Amino Acids with Cardioprotective

show abstract

“…15 Extensions of the methodology have been described to allow enantioselective preparation of cis and trans isomers of 3-or 5-alkyl-ACPCs. 16 and 6-alkyl-ACHCs, 17 as well as the pyrrolidine and tetrahydrofuran analogs of ACPC. 18 To date, however, the strategy has not been assessed as a route to smaller-ring β-AAs.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of an aza-Michael approach for the synthesis of 3,3-dimethyl-2-aminocyclobutane-1-carboxylic acid

Charnay‐Pouget¹,

Mathur²,

Baltaze³

et al. 2011

Arkivoc

View full text Add to dashboard Cite

The aza-Michael addition reaction of a dibenzylic amide anion with t-butyl 3,3-dimethylcyclobutene-1-carboxylate was investigated as a route to the title compound, a cyclic β-amino acid. In analogy with the known 5-and 6-membered ring homologues, the addition reaction proceeds smoothly, but with moderate diastereomeric and enantiomeric selectivities. The trans isomer of the title β-amino acid was obtained, for the first time, with a modest enantiomeric excess.

show abstract

Parallel kinetic resolution of tert-butyl (RS)-6-alkyl-cyclohex-1-ene-carboxylates for the asymmetric synthesis of 6-alkyl-substituted cishexacin derivatives

Cited by 32 publications

References 38 publications

Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

Parallel Kinetic Resolution of Acyclic γ-Amino-α,β-unsaturated Esters: Application to the Asymmetric Synthesis of 4-Aminopyrrolidin-2-ones

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

Evaluation of an aza-Michael approach for the synthesis of 3,3-dimethyl-2-aminocyclobutane-1-carboxylic acid

Contact Info

Product

Resources

About