Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base

Rosini, Goffredo; Paolucci, Claudio; Boschi, Francesca; Marotta, Emanuela; Righi, Paolo; Tozzi, Francesco

doi:10.1039/c0gc00013b

Cited by 15 publications

(9 citation statements)

References 61 publications

(10 reference statements)

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“…Paolucci et al published a series of conceptually interesting articles, describing application of (S)-Betti's base (95) in CIDT of α-branched aldehydes 96 a-l (Scheme 35). [86] At the outset, a reaction of 95 with racemic aldehydes 96 a-l furnished a precipitating 1:1 mixture of oxoaminals epi-97 a-l. Although the following CIDT is reported as a separate step for majority of the substrates, a one-pot setting was as well feasible (epi-97 f).…”

Section: Formation Of Schiff Base or Related Intermediatesmentioning

confidence: 99%

State of the Art in Crystallization‐Induced Diastereomer Transformations

Kolarovič

Jakubec

2021

Adv Synth Catal

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Crystallization-induced diastereomer transformations (CIDT) enable isolation of the target compounds in high enantio-and diastereomeric purities and with up to quantitative yields simply by filtration. Numerous inspiring examples of this appealing synthetic strategy reported over the last fifteen years are reviewed. Important observations along with aspects to consider when designing CIDT experiments are discussed. 3.3. Formation of Schiff Base or Related Intermediates 3.4. Aza-Michael and Mannich-Type Reactions 3.5. Strecker Reaction 3.6. Aldol Reactions 3.7. Epimerization at Phosphorus-Based Stereocenters 3.8. Racemization/Epimerization through Change of Conformation 3.9. Miscellaneous Examples of CIDT 4.Conclusions and Perspectives

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Section: Formation Of Schiff Base or Related Intermediatesmentioning

confidence: 99%

State of the Art in Crystallization‐Induced Diastereomer Transformations

Kolarovič

Jakubec

2021

Adv Synth Catal

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“…3-(4-Isopropylphenyl)-2-methylpropan-1-ol (14, 27% ee) [ 22 ]: 1 H NMR (500 MHz, CDCl 3 ) δ 7.15 (d, J = 8.0 Hz, 2H), 7.10 ( d, J = 8.0 Hz, 2H), 3.54 (dd, 5.0, 5.7 Hz, 1H), 3.47 (dd, J = 4.6, 6.1 Hz, 1H), 2.88 (m, 1H), 2.71 (dd, J = 6.5, 6.9 Hz, 1H), 2.41 (dd, J = 5.3, 8.1 Hz, 1H), 1.93 (m, 1H), 1.24 (d, J = 6.9 Hz, 6H), 0.92 (d, J = 6.5 Hz, 3H); 13 C NMR (125 MHz, CDCl 3 ) δ 146.4, 137.8, 129.0, 126.3, 67.8, 39.3, 37.8, 33.7, 24.1, 16.6; [α] D 25 = −2.3 ( c 0.15, CHCl 3 ); The enantiopurity was determined by HPLC (99:1 hexane/2-propanol; 1 mL/min; using a CHIRALPAK IC-3 column (0.46 cm Ø × 25 cm)): 17.6 min (minor) and 19.9 min (major).…”

Section: Methodsmentioning

confidence: 99%

Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution

Shibatomi¹,

Okimi²,

Abe³

et al. 2014

Beilstein J. Org. Chem.

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SummaryIn a previous study it was shown that the enantioselective α-fluorination of racemic α-chloroaldehydes with a chiral organocatalyst yielded the corresponding α-chloro-α-fluoroaldehydes with high enantioselectivity. It was also revealed that kinetic resolution of the starting aldehydes was involved in this asymmetric fluorination. This paper describes the determination of the absolute stereochemistry of a resulting α-chloro-α-fluoroaldehyde. Some information about the substrate scope and a possible reaction mechanism are also described which shed more light on the nature of this asymmetric fluorination reaction.

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“…There are papers dealing with the preparation of the enantiomers of 1c, 7,8 and the odour profiles of (+)-1c and (-)-1c have been reported. 9 Only recently, two different research groups have reported the preparation of enantioenriched cyclamal; 8,10 in particular, Kawasaki and co-workers have developed an enzymatic enantioselective synthesis of (R)-1d or (S)-1d and have described the olfactive profiles of the enantiomers. 10 In contrast, the olfactive notes of the enantiomers of 1a and 1b have not yet been reported.…”

Section: Figure 1 Arylpropanal Fragrancesmentioning

confidence: 99%

A Practical, Enantioselective Synthesis of the Fragrances Canthoxal and Silvial®, and Evaluation of Their Olfactory Activity

et al. 2014

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The fragrances (S)-(+)-and (R)-(-)-canthoxal [(S)-(+)-and (R)-(-)-3-(4-methoxyphenyl)-2-methylpropanal] and (+)-and (-)-Silvial ® [(+)-and (-)-3-(4-isobutylphenyl)-2-methylpropanal] have been synthesized in high enantiopurity via a simple four-step strategy starting from the commercially available 4-substituted benzaldehydes. The key synthetic step is the catalytic asymmetric hydrogenation of the appropriate 3-aryl-2-methylacrylic acid which has been carried out employing an in situ prepared ruthenium/axially chiral phosphine catalyst (up to 98% ee). The olfactory activity of the single enantiomers has been evaluated.

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Acid promoted CIDT for the deracemization of dihydrocinnamic aldehydes with Betti's base

Cited by 15 publications

References 61 publications

State of the Art in Crystallization‐Induced Diastereomer Transformations

State of the Art in Crystallization‐Induced Diastereomer Transformations

Organocatalytic asymmetric fluorination of α-chloroaldehydes involving kinetic resolution

A Practical, Enantioselective Synthesis of the Fragrances Canthoxal and Silvial®, and Evaluation of Their Olfactory Activity

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