Ligand-accelerated cadmium-catalyzed asymmetric allylation reactions in aqueous media

Chirality

Volumn 15, Issue 2, 2003, Pages 124-126

  Kobayashi, Shu ^a   Aoyama, Naohiro ^a   Manabe, Kei ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Allyltin; Aqueous reaction; Asymmetric catalysis; Chiral ligand; Ligand acceleration

Indexed keywords

ALDEHYDE; ALLYL TRIBUTYLTIN; BUTYLTIN DERIVATIVE; CADMIUM; DIAMINE; LIGAND; UNCLASSIFIED DRUG;

ALLYLATION; AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0037258680     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10154     Document Type: Article

References (25)

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2. For review, see: Yanagisawa A. Allylation of carbonyl groups. In: Jacobsen EN, Pfaltz A, Yamamoto H, editors. Comprehensive asymmetric catalysis, vol. II, chap. 27. Berlin: Springer; 1999. p 965-979.
3. For review, see: (a) Li CJ, Chan TH. Organic reactions in aqueous media. New York: John Wiley & Sons; 1997.
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6. (b) Loh TP. Xu J, Hu QY, Vittal JJ. A highly chemoselective and diastereoselective trifluoromethane sulfonic acid catalyzed addition of allyltributylstannanes to a steroidal aldehyde in aqueous media. Tetrahedron: Asymmetry 2000;11:1565-1569.
7. (c) Loh TP, Xu J. Trifluoromethane sulphonic acid: a Bronsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water. Tetrahedron Lett 1999;40:2431-2434.
8. (d) Yanagisawa A, Morodome M, Nakashima H, Yamamoto H. Allylation of aldehydes with allyltin compounds in acidic aqueous media - a catalytic version. Synlett 1997:1309-1311.
9. (e) Yanagisawa A, Nakashima H, Ishiba A, Yamamoto H. Catalytic asymmetric allylation of aldehydes using a chiral silver(I) complex. J Am Chem Soc 1996;118:4723-4724.
10. (f) Hachiya I, Kobayshi S. Aqueous reactions with a Lewis acid and an organometallic reagent. The scandium trifluoromethanesulfonate-catalyzed allylation reaction of carbonyl compounds with tetraallyltin. J Org Chem 1993;58:6958-6960.
11. 3-catalyzed allylation reactions of aldehydes in micellar systems. Chem Lett 1997:831-832.
12. Loh TP, Zhou JR. A catalytic enantioselective allylation reaction of aldehydes in an aqueous medium. Tetrahedron Lett 2000;41:5261-5264.
13. Kobayashi S, Aoyama N, Manabe K. Ligand-accelerated cadmium-catalyzed allylation of aldehydes and ketones in aqueous media. Synlett 2002;483-485.
14. For review, see: (a) Berrisford DJ, Bolm C, Sharpless KB. Ligand-accelerated catalysis. Angew Chem Int Ed Engl 1995;34:1059-1070. Cf. For ligand effects on Diels-Alder reaction in water, see: (b) Otto S, Engberts JBFN. A systematic study of ligand effects on a Lewis-acid-catalyzed Diels-Alder reaction in water. Water-enhanced enantioselectivity. J Am Chem Soc 1999;121:6798-6806.
15. For review, see: (a) Berrisford DJ, Bolm C, Sharpless KB. Ligand-accelerated catalysis. Angew Chem Int Ed Engl 1995;34:1059-1070. Cf. For ligand effects on Diels-Alder reaction in water, see: (b) Otto S, Engberts JBFN. A systematic study of ligand effects on a Lewis-acid-catalyzed Diels-Alder reaction in water. Water-enhanced enantioselectivity. J Am Chem Soc 1999;121:6798-6806.
16. 1a: (a) Haiza MA, Sanyal A, Snyder JK. O-Nitromandelic acid: a chiral solvating agent for the NMR determination of chiral diamine enanfiomeric purity. Chirality 1997;9:556-562. 1b, 1c, 1e: (b) Kobayashi S, Matsubara R, Kitagawa H. Catalytic asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12. Org Lett 2002;4:143-145. 1d: (c) Mimoun H, Laumer JYS, Giannini L, Scopelliti R, Floriani C. Enantioselective reduction of ketones by polymethylhydrosiloxane in the presence of chiral zinc catalysts. J Am Chem Soc 1999;121:6158-6166. 1g: (d) Corey EJ, Jardine PDS, Virgil S, Yuen PW, Connell RD. Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetraoxide. An effective controller system and a rational mechanistic model. J Am Chem Soc 1989;111:9243-9244. For a recent work using ligand 1 in aqueous media, see: (e) Kobayashi S, Hamada T, Manabe K. The catalytic asymmetric Mannich-type reactions in aqueous media. J Am Chem Soc 2002;124:5640-5641.
17. 1a: (a) Haiza MA, Sanyal A, Snyder JK. O-Nitromandelic acid: a chiral solvating agent for the NMR determination of chiral diamine enanfiomeric purity. Chirality 1997;9:556-562. 1b, 1c, 1e: (b) Kobayashi S, Matsubara R, Kitagawa H. Catalytic asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12. Org Lett 2002;4:143-145. 1d: (c) Mimoun H, Laumer JYS, Giannini L, Scopelliti R, Floriani C. Enantioselective reduction of ketones by polymethylhydrosiloxane in the presence of chiral zinc catalysts. J Am Chem Soc 1999;121:6158-6166. 1g: (d) Corey EJ, Jardine PDS, Virgil S, Yuen PW, Connell RD. Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetraoxide. An effective controller system and a rational mechanistic model. J Am Chem Soc 1989;111:9243-9244. For a recent work using ligand 1 in aqueous media, see: (e) Kobayashi S, Hamada T, Manabe K. The catalytic asymmetric Mannich-type reactions in aqueous media. J Am Chem Soc 2002;124:5640-5641.
18. 1a: (a) Haiza MA, Sanyal A, Snyder JK. O-Nitromandelic acid: a chiral solvating agent for the NMR determination of chiral diamine enanfiomeric purity. Chirality 1997;9:556-562. 1b, 1c, 1e: (b) Kobayashi S, Matsubara R, Kitagawa H. Catalytic asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12. Org Lett 2002;4:143-145. 1d: (c) Mimoun H, Laumer JYS, Giannini L, Scopelliti R, Floriani C. Enantioselective reduction of ketones by polymethylhydrosiloxane in the presence of chiral zinc catalysts. J Am Chem Soc 1999;121:6158-6166. 1g: (d) Corey EJ, Jardine PDS, Virgil S, Yuen PW, Connell RD. Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetraoxide. An effective controller system and a rational mechanistic model. J Am Chem Soc 1989;111:9243-9244. For a recent work using ligand 1 in aqueous media, see: (e) Kobayashi S, Hamada T, Manabe K. The catalytic asymmetric Mannich-type reactions in aqueous media. J Am Chem Soc 2002;124:5640-5641.
19. 1a: (a) Haiza MA, Sanyal A, Snyder JK. O-Nitromandelic acid: a chiral solvating agent for the NMR determination of chiral diamine enanfiomeric purity. Chirality 1997;9:556-562. 1b, 1c, 1e: (b) Kobayashi S, Matsubara R, Kitagawa H. Catalytic asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12. Org Lett 2002;4:143-145. 1d: (c) Mimoun H, Laumer JYS, Giannini L, Scopelliti R, Floriani C. Enantioselective reduction of ketones by polymethylhydrosiloxane in the presence of chiral zinc catalysts. J Am Chem Soc 1999;121:6158-6166. 1g: (d) Corey EJ, Jardine PDS, Virgil S, Yuen PW, Connell RD. Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetraoxide. An effective controller system and a rational mechanistic model. J Am Chem Soc 1989;111:9243-9244. For a recent work using ligand 1 in aqueous media, see: (e) Kobayashi S, Hamada T, Manabe K. The catalytic asymmetric Mannich-type reactions in aqueous media. J Am Chem Soc 2002;124:5640-5641.
20. 1a: (a) Haiza MA, Sanyal A, Snyder JK. O-Nitromandelic acid: a chiral solvating agent for the NMR determination of chiral diamine enanfiomeric purity. Chirality 1997;9:556-562. 1b, 1c, 1e: (b) Kobayashi S, Matsubara R, Kitagawa H. Catalytic asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12. Org Lett 2002;4:143-145. 1d: (c) Mimoun H, Laumer JYS, Giannini L, Scopelliti R, Floriani C. Enantioselective reduction of ketones by polymethylhydrosiloxane in the presence of chiral zinc catalysts. J Am Chem Soc 1999;121:6158-6166. 1g: (d) Corey EJ, Jardine PDS, Virgil S, Yuen PW, Connell RD. Enantioselective vicinal hydroxylation of terminal and E-1,2-disubstituted olefins by a chiral complex of osmium tetraoxide. An effective controller system and a rational mechanistic model. J Am Chem Soc 1989;111:9243-9244. For a recent work using ligand 1 in aqueous media, see: (e) Kobayashi S, Hamada T, Manabe K. The catalytic asymmetric Mannich-type reactions in aqueous media. J Am Chem Soc 2002;124:5640-5641.
21. The absolute configurations were determined by the following studies. Table 2, entry 1: (a) Sugimoto K, Aoyagi S, Kibayashi C. Enantioselective allylation of aldehydes with (dialkoxyallyl) chromium (III) complexes. J Org Chem 1997;62:2322-2323. entries 2, 3: (b) Denmark SE, Coe DM, Pratt NE, Griedel BD. Asymmetric allylation of aldehydes with chiral Lewis bases. J Org Chem 1994;59:6161-6163. entries 4, 7: (c) Minowa N, Mukaiyama T. Asymmetric allylation with a new chiral allylating agent prepared from tin(II) triflate, chiral diamine, and allylaluminum. Bull Chem Soc Jpn 1987;60:3697-3704. entry 6: (d) Uenishi J, Hiraoka T, Hata S, Nishiwaki K, Yonemitsu O. Chiral pyridines: optical resolution of 1-(2-pyridyl)- and 1-[6-(2,2′-bipyridyl)]ethanols by lipase-catalyzed enantioselective acetylation. J Org Chem 1998;63:2481-2487. entry 8: (e) Roush WR, Hoong LK, Palmer MAJ, Park JC. Asymmetric synthesis using tartrate ester modified allylboronates. 1. Factors influencing stereoselectivity. J Org Chem 1990;55:4109-4117.
22. The absolute configurations were determined by the following studies. Table 2, entry 1: (a) Sugimoto K, Aoyagi S, Kibayashi C. Enantioselective allylation of aldehydes with (dialkoxyallyl) chromium (III) complexes. J Org Chem 1997;62:2322-2323. entries 2, 3: (b) Denmark SE, Coe DM, Pratt NE, Griedel BD. Asymmetric allylation of aldehydes with chiral Lewis bases. J Org Chem 1994;59:6161-6163. entries 4, 7: (c) Minowa N, Mukaiyama T. Asymmetric allylation with a new chiral allylating agent prepared from tin(II) triflate, chiral diamine, and allylaluminum. Bull Chem Soc Jpn 1987;60:3697-3704. entry 6: (d) Uenishi J, Hiraoka T, Hata S, Nishiwaki K, Yonemitsu O. Chiral pyridines: optical resolution of 1-(2-pyridyl)- and 1-[6-(2,2′-bipyridyl)]ethanols by lipase-catalyzed enantioselective acetylation. J Org Chem 1998;63:2481-2487. entry 8: (e) Roush WR, Hoong LK, Palmer MAJ, Park JC. Asymmetric synthesis using tartrate ester modified allylboronates. 1. Factors influencing stereoselectivity. J Org Chem 1990;55:4109-4117.
23. The absolute configurations were determined by the following studies. Table 2, entry 1: (a) Sugimoto K, Aoyagi S, Kibayashi C. Enantioselective allylation of aldehydes with (dialkoxyallyl) chromium (III) complexes. J Org Chem 1997;62:2322-2323. entries 2, 3: (b) Denmark SE, Coe DM, Pratt NE, Griedel BD. Asymmetric allylation of aldehydes with chiral Lewis bases. J Org Chem 1994;59:6161-6163. entries 4, 7: (c) Minowa N, Mukaiyama T. Asymmetric allylation with a new chiral allylating agent prepared from tin(II) triflate, chiral diamine, and allylaluminum. Bull Chem Soc Jpn 1987;60:3697-3704. entry 6: (d) Uenishi J, Hiraoka T, Hata S, Nishiwaki K, Yonemitsu O. Chiral pyridines: optical resolution of 1-(2-pyridyl)- and 1-[6-(2,2′-bipyridyl)]ethanols by lipase-catalyzed enantioselective acetylation. J Org Chem 1998;63:2481-2487. entry 8: (e) Roush WR, Hoong LK, Palmer MAJ, Park JC. Asymmetric synthesis using tartrate ester modified allylboronates. 1. Factors influencing stereoselectivity. J Org Chem 1990;55:4109-4117.
24. The absolute configurations were determined by the following studies. Table 2, entry 1: (a) Sugimoto K, Aoyagi S, Kibayashi C. Enantioselective allylation of aldehydes with (dialkoxyallyl) chromium (III) complexes. J Org Chem 1997;62:2322-2323. entries 2, 3: (b) Denmark SE, Coe DM, Pratt NE, Griedel BD. Asymmetric allylation of aldehydes with chiral Lewis bases. J Org Chem 1994;59:6161-6163. entries 4, 7: (c) Minowa N, Mukaiyama T. Asymmetric allylation with a new chiral allylating agent prepared from tin(II) triflate, chiral diamine, and allylaluminum. Bull Chem Soc Jpn 1987;60:3697-3704. entry 6: (d) Uenishi J, Hiraoka T, Hata S, Nishiwaki K, Yonemitsu O. Chiral pyridines: optical resolution of 1-(2-pyridyl)- and 1-[6-(2,2′-bipyridyl)]ethanols by lipase-catalyzed enantioselective acetylation. J Org Chem 1998;63:2481-2487. entry 8: (e) Roush WR, Hoong LK, Palmer MAJ, Park JC. Asymmetric synthesis using tartrate ester modified allylboronates. 1. Factors influencing stereoselectivity. J Org Chem 1990;55:4109-4117.
25. The absolute configurations were determined by the following studies. Table 2, entry 1: (a) Sugimoto K, Aoyagi S, Kibayashi C. Enantioselective allylation of aldehydes with (dialkoxyallyl) chromium (III) complexes. J Org Chem 1997;62:2322-2323. entries 2, 3: (b) Denmark SE, Coe DM, Pratt NE, Griedel BD. Asymmetric allylation of aldehydes with chiral Lewis bases. J Org Chem 1994;59:6161-6163. entries 4, 7: (c) Minowa N, Mukaiyama T. Asymmetric allylation with a new chiral allylating agent prepared from tin(II) triflate, chiral diamine, and allylaluminum. Bull Chem Soc Jpn 1987;60:3697-3704. entry 6: (d) Uenishi J, Hiraoka T, Hata S, Nishiwaki K, Yonemitsu O. Chiral pyridines: optical resolution of 1-(2-pyridyl)- and 1-[6-(2,2′-bipyridyl)]ethanols by lipase-catalyzed enantioselective acetylation. J Org Chem 1998;63:2481-2487. entry 8: (e) Roush WR, Hoong LK, Palmer MAJ, Park JC. Asymmetric synthesis using tartrate ester modified allylboronates. 1. Factors influencing stereoselectivity. J Org Chem 1990;55:4109-4117.