Chiral Aldehydes in Hydrocarbons: Diastereoselective Nucleophilic Addition, NMR, and CD Spectroscopy Reveal Dynamic Solvation Effects

Chirality

Volumn 16, Issue 1, 2004, Pages 50-56

  Cainelli, Gianfranco ^a   Galletti, Paola ^a   Pieraccini, Silvia ^a   Quintavalla, Arianna ^a   Giacomini, Daria ^a   Spada, Gian Piero ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Circular dichroism; Inversion temperature; Nuclear magnetic resonance; Solvent effect; Ultraviolet spectroscopy

Indexed keywords

2 PHENYLPROPIONALDEHYDE; ALDEHYDE DERIVATIVE; DECANE; DODECANE; HYDROCARBON; LACTIC ACID DERIVATIVE; MANDELIC ACID DERIVATIVE; O (TERT BUTYL DIMETHYLSILLYL)LACTAL; O (TERT BUTYL DIMETHYLSILYL)MANDELIC ALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SOLVATION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0348014422     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10310     Document Type: Article

References (59)

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9. For recent examples: Roland S, Mangeney P. Addition of Grignard reagents to chiral 1,2-bisimines: a diasteroselective preparation of unsymmetrical 1,2-diamines. Eur J Org Chem 2000;611-616. Cainelli G, Giacomini D, Galletti P. Reversal of diastereofacial selectivity in the n-butyllithium addition to O-protected N-trimethylsilylimines of (2S)-lactal. Enthalpic versus entropic contributions. Eur J Org Chem 1999;61-65. Crimmins MT, Choy AL, Allison L. Solvent effects on diastereoselective intramolecular [2 + 2] photocycloadditions: reversal of selectivity through intramolecular hydrogen bonding. J Am Chem Soc 1997;119:10237-10238. Murray RW, Singh M, Williams BL, Moncrieff HM. Solvent tuning of diastereoselectivity in dimethyldioxirane epoxidation reactions. Tetrahedron Lett 1995;36:2437-2440. Naraku G, Hori K, Ito YN, Katsuki T. Remarkable solvent effect on the enantioface selectivity in the Diels-Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative. Tetrahedron Lett 1997;38:8231-8232. Wipf P, Jung J-K. Long-range electrostatic effects in synthesis: dipole-controlled nucleophilic addition to a naphthoquinone acetal in model studies toward diepoxin σ. Angew Chem 1997;109:785-788; Angew Chem Int Ed Engl 1997;36:764-767. Denmark SE, Nakajima N, Nicaise OJC. Asymmetric addition of organolithium reagents to imines. J Am Chem Soc 1994;116:8797-8798. Reetz MT, Stanchev S, Haning H. Cram selectivity in the reaction of 2-phenylpropanal with alkyllithium reagents: myth and reality. Tetrahedron 1992;48:6813-6820.
10. For recent examples: Roland S, Mangeney P. Addition of Grignard reagents to chiral 1,2-bisimines: a diasteroselective preparation of unsymmetrical 1,2-diamines. Eur J Org Chem 2000;611-616. Cainelli G, Giacomini D, Galletti P. Reversal of diastereofacial selectivity in the n-butyllithium addition to O-protected N-trimethylsilylimines of (2S)-lactal. Enthalpic versus entropic contributions. Eur J Org Chem 1999;61-65. Crimmins MT, Choy AL, Allison L. Solvent effects on diastereoselective intramolecular [2 + 2] photocycloadditions: reversal of selectivity through intramolecular hydrogen bonding. J Am Chem Soc 1997;119:10237-10238. Murray RW, Singh M, Williams BL, Moncrieff HM. Solvent tuning of diastereoselectivity in dimethyldioxirane epoxidation reactions. Tetrahedron Lett 1995;36:2437-2440. Naraku G, Hori K, Ito YN, Katsuki T. Remarkable solvent effect on the enantioface selectivity in the Diels-Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative. Tetrahedron Lett 1997;38:8231-8232. Wipf P, Jung J-K. Long-range electrostatic effects in synthesis: dipole-controlled nucleophilic addition to a naphthoquinone acetal in model studies toward diepoxin σ. Angew Chem 1997;109:785-788; Angew Chem Int Ed Engl 1997;36:764-767. Denmark SE, Nakajima N, Nicaise OJC. Asymmetric addition of organolithium reagents to imines. J Am Chem Soc 1994;116:8797-8798. Reetz MT, Stanchev S, Haning H. Cram selectivity in the reaction of 2-phenylpropanal with alkyllithium reagents: myth and reality. Tetrahedron 1992;48:6813-6820.
11. For recent examples: Roland S, Mangeney P. Addition of Grignard reagents to chiral 1,2-bisimines: a diasteroselective preparation of unsymmetrical 1,2-diamines. Eur J Org Chem 2000;611-616. Cainelli G, Giacomini D, Galletti P. Reversal of diastereofacial selectivity in the n-butyllithium addition to O-protected N-trimethylsilylimines of (2S)-lactal. Enthalpic versus entropic contributions. Eur J Org Chem 1999;61-65. Crimmins MT, Choy AL, Allison L. Solvent effects on diastereoselective intramolecular [2 + 2] photocycloadditions: reversal of selectivity through intramolecular hydrogen bonding. J Am Chem Soc 1997;119:10237-10238. Murray RW, Singh M, Williams BL, Moncrieff HM. Solvent tuning of diastereoselectivity in dimethyldioxirane epoxidation reactions. Tetrahedron Lett 1995;36:2437-2440. Naraku G, Hori K, Ito YN, Katsuki T. Remarkable solvent effect on the enantioface selectivity in the Diels-Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative. Tetrahedron Lett 1997;38:8231-8232. Wipf P, Jung J-K. Long-range electrostatic effects in synthesis: dipole-controlled nucleophilic addition to a naphthoquinone acetal in model studies toward diepoxin σ. Angew Chem 1997;109:785-788; Angew Chem Int Ed Engl 1997;36:764-767. Denmark SE, Nakajima N, Nicaise OJC. Asymmetric addition of organolithium reagents to imines. J Am Chem Soc 1994;116:8797-8798. Reetz MT, Stanchev S, Haning H. Cram selectivity in the reaction of 2-phenylpropanal with alkyllithium reagents: myth and reality. Tetrahedron 1992;48:6813-6820.
12. For recent examples: Roland S, Mangeney P. Addition of Grignard reagents to chiral 1,2-bisimines: a diasteroselective preparation of unsymmetrical 1,2-diamines. Eur J Org Chem 2000;611-616. Cainelli G, Giacomini D, Galletti P. Reversal of diastereofacial selectivity in the n-butyllithium addition to O-protected N-trimethylsilylimines of (2S)-lactal. Enthalpic versus entropic contributions. Eur J Org Chem 1999;61-65. Crimmins MT, Choy AL, Allison L. Solvent effects on diastereoselective intramolecular [2 + 2] photocycloadditions: reversal of selectivity through intramolecular hydrogen bonding. J Am Chem Soc 1997;119:10237-10238. Murray RW, Singh M, Williams BL, Moncrieff HM. Solvent tuning of diastereoselectivity in dimethyldioxirane epoxidation reactions. Tetrahedron Lett 1995;36:2437-2440. Naraku G, Hori K, Ito YN, Katsuki T. Remarkable solvent effect on the enantioface selectivity in the Diels-Alder reaction catalyzed by an aluminum complex of a newly prepared chiral menthol derivative. Tetrahedron Lett 1997;38:8231-8232. Wipf P, Jung J-K. Long-range electrostatic effects in synthesis: dipole-controlled nucleophilic addition to a naphthoquinone acetal in model studies toward diepoxin σ. Angew Chem 1997;109:785-788; Angew Chem Int Ed Engl 1997;36:764-767. Denmark SE, Nakajima N, Nicaise OJC. Asymmetric addition of organolithium reagents to imines. J Am Chem Soc 1994;116:8797-8798. Reetz MT, Stanchev S, Haning H. Cram selectivity in the reaction of 2-phenylpropanal with alkyllithium reagents: myth and reality. Tetrahedron 1992;48:6813-6820.
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43. Cainelli G, Galletti P, Giacomini D, Orioli P. Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenylpropanal: enthalpy and entropy contribution. Tetrahedron Lett 2001;42:7383-7385. Lombardo M, Frabboni S, Trombini C. Entropy-controlled selectivity in the vinylation of a cyclic chiral nitrone. An efficient route to enantiopure polyhydroxylated pyrrolidines. J Org Chem 2001;66:1264-1268. Filippi A, Trout NA, Brunelle P, Adcock W, Sorensen TS, Speranza M. Origin of diastereofacial selectivity in tertiary 2-adamantyl cations. J Am Chem Soc 2001;123:6396-6403. Sugimura T, Hagiya K, Sato Y, Tei T, Tai A, Okuyama T. Entropy-controlled asymmetric synthesis. How differential activation entropy is induced in chiral tethered reactions. Org Lett 2001;3:37-40; Inoue Y, Ikeda H, Kaneda M, Sumimura T, Everitt SRL, Wada T. Entropy-controlled asymmetric photochemistry: switching of product chirality by solvent. J Am Chem Soc 2000;122:406-407. Rosenberg RE, Vilardo JS. The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride. Tetrahedron Lett 1996;37:2185-2188. Giese B. The isoselective relationship. Acc Chem Res 1984;17:438-442.
44. Cainelli G, Galletti P, Giacomini D, Orioli P. Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenylpropanal: enthalpy and entropy contribution. Tetrahedron Lett 2001;42:7383-7385. Lombardo M, Frabboni S, Trombini C. Entropy-controlled selectivity in the vinylation of a cyclic chiral nitrone. An efficient route to enantiopure polyhydroxylated pyrrolidines. J Org Chem 2001;66:1264-1268. Filippi A, Trout NA, Brunelle P, Adcock W, Sorensen TS, Speranza M. Origin of diastereofacial selectivity in tertiary 2-adamantyl cations. J Am Chem Soc 2001;123:6396-6403. Sugimura T, Hagiya K, Sato Y, Tei T, Tai A, Okuyama T. Entropy-controlled asymmetric synthesis. How differential activation entropy is induced in chiral tethered reactions. Org Lett 2001;3:37-40; Inoue Y, Ikeda H, Kaneda M, Sumimura T, Everitt SRL, Wada T. Entropy-controlled asymmetric photochemistry: switching of product chirality by solvent. J Am Chem Soc 2000;122:406-407. Rosenberg RE, Vilardo JS. The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride. Tetrahedron Lett 1996;37:2185-2188. Giese B. The isoselective relationship. Acc Chem Res 1984;17:438-442.
45. Cainelli G, Galletti P, Giacomini D, Orioli P. Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenylpropanal: enthalpy and entropy contribution. Tetrahedron Lett 2001;42:7383-7385. Lombardo M, Frabboni S, Trombini C. Entropy-controlled selectivity in the vinylation of a cyclic chiral nitrone. An efficient route to enantiopure polyhydroxylated pyrrolidines. J Org Chem 2001;66:1264-1268. Filippi A, Trout NA, Brunelle P, Adcock W, Sorensen TS, Speranza M. Origin of diastereofacial selectivity in tertiary 2-adamantyl cations. J Am Chem Soc 2001;123:6396-6403. Sugimura T, Hagiya K, Sato Y, Tei T, Tai A, Okuyama T. Entropy-controlled asymmetric synthesis. How differential activation entropy is induced in chiral tethered reactions. Org Lett 2001;3:37-40; Inoue Y, Ikeda H, Kaneda M, Sumimura T, Everitt SRL, Wada T. Entropy-controlled asymmetric photochemistry: switching of product chirality by solvent. J Am Chem Soc 2000;122:406-407. Rosenberg RE, Vilardo JS. The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride. Tetrahedron Lett 1996;37:2185-2188. Giese B. The isoselective relationship. Acc Chem Res 1984;17:438-442.
46. Cainelli G, Galletti P, Giacomini D, Orioli P. Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenylpropanal: enthalpy and entropy contribution. Tetrahedron Lett 2001;42:7383-7385. Lombardo M, Frabboni S, Trombini C. Entropy-controlled selectivity in the vinylation of a cyclic chiral nitrone. An efficient route to enantiopure polyhydroxylated pyrrolidines. J Org Chem 2001;66:1264-1268. Filippi A, Trout NA, Brunelle P, Adcock W, Sorensen TS, Speranza M. Origin of diastereofacial selectivity in tertiary 2-adamantyl cations. J Am Chem Soc 2001;123:6396-6403. Sugimura T, Hagiya K, Sato Y, Tei T, Tai A, Okuyama T. Entropy-controlled asymmetric synthesis. How differential activation entropy is induced in chiral tethered reactions. Org Lett 2001;3:37-40; Inoue Y, Ikeda H, Kaneda M, Sumimura T, Everitt SRL, Wada T. Entropy-controlled asymmetric photochemistry: switching of product chirality by solvent. J Am Chem Soc 2000;122:406-407. Rosenberg RE, Vilardo JS. The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride. Tetrahedron Lett 1996;37:2185-2188. Giese B. The isoselective relationship. Acc Chem Res 1984;17:438-442.
47. Cainelli G, Galletti P, Giacomini D, Orioli P. Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenylpropanal: enthalpy and entropy contribution. Tetrahedron Lett 2001;42:7383-7385. Lombardo M, Frabboni S, Trombini C. Entropy-controlled selectivity in the vinylation of a cyclic chiral nitrone. An efficient route to enantiopure polyhydroxylated pyrrolidines. J Org Chem 2001;66:1264-1268. Filippi A, Trout NA, Brunelle P, Adcock W, Sorensen TS, Speranza M. Origin of diastereofacial selectivity in tertiary 2-adamantyl cations. J Am Chem Soc 2001;123:6396-6403. Sugimura T, Hagiya K, Sato Y, Tei T, Tai A, Okuyama T. Entropy-controlled asymmetric synthesis. How differential activation entropy is induced in chiral tethered reactions. Org Lett 2001;3:37-40; Inoue Y, Ikeda H, Kaneda M, Sumimura T, Everitt SRL, Wada T. Entropy-controlled asymmetric photochemistry: switching of product chirality by solvent. J Am Chem Soc 2000;122:406-407. Rosenberg RE, Vilardo JS. The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride. Tetrahedron Lett 1996;37:2185-2188. Giese B. The isoselective relationship. Acc Chem Res 1984;17:438-442.
48. Cainelli G, Galletti P, Giacomini D, Orioli P. Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenylpropanal: enthalpy and entropy contribution. Tetrahedron Lett 2001;42:7383-7385. Lombardo M, Frabboni S, Trombini C. Entropy-controlled selectivity in the vinylation of a cyclic chiral nitrone. An efficient route to enantiopure polyhydroxylated pyrrolidines. J Org Chem 2001;66:1264-1268. Filippi A, Trout NA, Brunelle P, Adcock W, Sorensen TS, Speranza M. Origin of diastereofacial selectivity in tertiary 2-adamantyl cations. J Am Chem Soc 2001;123:6396-6403. Sugimura T, Hagiya K, Sato Y, Tei T, Tai A, Okuyama T. Entropy-controlled asymmetric synthesis. How differential activation entropy is induced in chiral tethered reactions. Org Lett 2001;3:37-40; Inoue Y, Ikeda H, Kaneda M, Sumimura T, Everitt SRL, Wada T. Entropy-controlled asymmetric photochemistry: switching of product chirality by solvent. J Am Chem Soc 2000;122:406-407. Rosenberg RE, Vilardo JS. The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride. Tetrahedron Lett 1996;37:2185-2188. Giese B. The isoselective relationship. Acc Chem Res 1984;17:438-442.
49. Cainelli G, Galletti P, Giacomini D, Orioli P. Solvent and temperature effect in aldol condensation between the lithium enolate of tert-butyl acetate and 2-phenylpropanal: enthalpy and entropy contribution. Tetrahedron Lett 2001;42:7383-7385. Lombardo M, Frabboni S, Trombini C. Entropy-controlled selectivity in the vinylation of a cyclic chiral nitrone. An efficient route to enantiopure polyhydroxylated pyrrolidines. J Org Chem 2001;66:1264-1268. Filippi A, Trout NA, Brunelle P, Adcock W, Sorensen TS, Speranza M. Origin of diastereofacial selectivity in tertiary 2-adamantyl cations. J Am Chem Soc 2001;123:6396-6403. Sugimura T, Hagiya K, Sato Y, Tei T, Tai A, Okuyama T. Entropy-controlled asymmetric synthesis. How differential activation entropy is induced in chiral tethered reactions. Org Lett 2001;3:37-40; Inoue Y, Ikeda H, Kaneda M, Sumimura T, Everitt SRL, Wada T. Entropy-controlled asymmetric photochemistry: switching of product chirality by solvent. J Am Chem Soc 2000;122:406-407. Rosenberg RE, Vilardo JS. The importance of entropy in stereoselection. Reduction of tert-butylcyclohexanone by lithium aluminum hydride. Tetrahedron Lett 1996;37:2185-2188. Giese B. The isoselective relationship. Acc Chem Res 1984;17:438-442.
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51. For solvent effects on chemical shift, see, for instance: Helgaker T, Jaszunski M, Ruud K. Ab initio methods for the calculation of NMR shielding and indirect spin-spin coupling constants. Chem Rev 1999;99:293-352. Lau EY, Gerig JT. Solvent effects on fluorine shielding in fluorobenzene. J Am Chem Soc 1996;118:1194-1193. Lau EY, Gerig JT. Solvent effects on nuclear shielding of neon. J Chem Phys 1995;103:3341-3349, and references therein.
52. For solvent effects on chemical shift, see, for instance: Helgaker T, Jaszunski M, Ruud K. Ab initio methods for the calculation of NMR shielding and indirect spin-spin coupling constants. Chem Rev 1999;99:293-352. Lau EY, Gerig JT. Solvent effects on fluorine shielding in fluorobenzene. J Am Chem Soc 1996;118:1194-1193. Lau EY, Gerig JT. Solvent effects on nuclear shielding of neon. J Chem Phys 1995;103:3341-3349, and references therein.
53. For a recent comprehensive book on circular dichroism, see: Berova N, Nakanishi K, Woody RW (eds.). Circular dichroism - principles and applications. New York: Wiley-VCH; 2000.
54. Gergely A. Application of circular dichroism spectropolarimetry to the determination of steroids, In: Purdie N, Brittain HG, editors. Analytical application of circular dichroism. Amsterdam: Elsevier; 1994.
55. Bosnich B. Asymmetric syntheses, asymmetric transformations, and asymmetric inductions in an optically active solvent. J Am Chem Soc 1967;89:6143-6148. Schipper PE, O'Brien JM, Ridley DD. Dispersion-induced circular dichroism spectra of benzophenone and fluorenone in chiral solutions. J Phys Chem 1985;89:5805.
56. Bosnich B. Asymmetric syntheses, asymmetric transformations, and asymmetric inductions in an optically active solvent. J Am Chem Soc 1967;89:6143-6148. Schipper PE, O'Brien JM, Ridley DD. Dispersion-induced circular dichroism spectra of benzophenone and fluorenone in chiral solutions. J Phys Chem 1985;89:5805.
57. Miller JC, Miller JN. Statistics for analytical chemistry. 3rd ed. Chichester, UK: Ellis Horwood PTR Prentice Hall; 1993.
58. See Ref. 8 and Cainelli G, De Matteis V, Galletti P, Giacomini D, Orioli P. Temperature and solvent effect on enzyme stereoselectivity: inversion temperature in kinetic resolutions with lipases. Chem Commun 2000;2351-2352.
59. Cainelli G, Giacomin D, Galletti P, Orioli P, Paradisi F. Diastereofacial selectivity of O-protected α-hydroxy aldehydes: temperature and solvent effect. Eur J Org Chem 2000;3619-3626.