Asymmetric reductive aldol-type reaction with carbonyl compounds using dialkyl tartrate as a chiral ligand

Chemical and Pharmaceutical Bulletin

Volumn 62, Issue 10, 2014, Pages 956-961

  Isoda, Motoyuki ^a   Sato, Kazuyuki ^a   Tokura, Yoriko ^a   Tarui, Atsushi ^a   Omote, Masaaki ^a   Ando, Akira ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

Aldol type cyclization; Asymmetric reaction; Biszinc tartrate complex; Reductive aldol type reaction; RhCl(PPh3)3

Indexed keywords

CARBONYL DERIVATIVE; TARTARIC ACID; 3-HYDROXYBUTANAL; ALDEHYDE; COORDINATION COMPOUND; ESTER; KETONE; LIGAND; RHODIUM; TARTARIC ACID DERIVATIVE; ZINC;

ALDOL REACTION; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; LIGAND BINDING; REDUCTION; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; CATALYSIS; COORDINATION COMPLEXES; CYCLIZATION; ESTERS; KETONES; LIGANDS; RHODIUM; STEREOISOMERISM; TARTRATES; ZINC;

EID: 84908221747     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c14-00223     Document Type: Article

References (29)

1. McGuire J. M., Bunch R. L., Anderson R. C., Boaz H. E., Flynn E. H., Powell H. M., Smith J. W., Antibiot. Chemother., 2, 281-283 (1952).
2. Dunetz J. R., Julian L. D., Newcom J. S., Roush W. R., J. Am. Chem. Soc., 130, 16407-16416 (2008).
3. Smith A. B. III, Beauchamp T. J., LaMarche M. J., Kaufman M. D., Qiu Y., Arimoto H., Jones D. R., Kobayashi K., J. Am. Chem. Soc., 122, 8654-8664 (2000).
4. Revis A., Hilty T. K., Tetrahedron Lett., 28, 4809-4812 (1987).
5. Willis M. C., Woodward R. L., J. Am. Chem. Soc., 127, 18012-18013 (2005).
6. Isayama S., Mukaiyama T., Chem. Lett., 18, 2005-2008 (1989).
7. Baik T. G., Luis A. L., Wang L. C., Krische M. J., J. Am. Chem. Soc., 123, 5112-5113 (2001).
8. Wang L. C., Jang H.-Y., Roh Y., Lynch V., Schultz A. J., Wang X., Krische M. J., J. Am. Chem. Soc., 124, 9448-9453 (2002).
9. Lam H. W., Joensuu P. M., Murray G. J., Fordyce E. A. F., Prieto O., Luebbers T., Org. Lett., 8, 3729-3732 (2006).
10. Lumby R. J. R., Joensuu P. M., Lam H. W., Org. Lett., 9, 4367-4370 (2007).
11. Ooi T., Doda K., Sakai D., Maruoka K., Tetrahedron Lett., 40, 2133-2136 (1999).
12. Welle A., Díez-González S., Tinant B., Nolan S. P., Riant O., Org. Lett., 8, 6059-6062 (2006).
13. Lam H. W., Joensuu P. M. A., Org. Lett., 7, 4225-4228 (2005).
14. Nishiyama H., Shiomi T., Tsuchiya Y., Matsuda I., J. Am. Chem. Soc., 127, 6972-6973 (2005).
15. Deschamp J., Chuzel O., Hannedouche J., Riant O., Angew. Chem. Int. Ed., 45, 1292-1297 (2006).
16. Hashimoto T., Ito J., Nishiyama H., Tetrahedron, 64, 9408-9412 (2008).
17. Shiomi T., Adachi T., Ito J., Nishiyama H., Org. Lett., 11, 1011-1014 (2009).
18. Kanai K., Wakabayashi H., Honda T., Org. Lett., 2, 2549-2551 (2000).
19. Sato K., Tarui A., Kita T., Ishida Y., Tamura H., Omote M., Ando A., Kumadaki I., Tetrahedron Lett., 45, 5735-5737 (2004).
20. Sato K., Isoda M., Ohata S., Morita S., Tarui A., Omote M., Kumadaki I., Ando A., Adv. Synth. Catal., 354, 510-514 (2012).
21. Sato K., Isoda M., Tokura Y., Omura K., Tarui A., Omote M., Kumadaki I., Ando A., Tetrahedron Lett., 54, 5913-5915 (2013).
22. Russell A. E., Fuller O. N., Taylor J. S., Aurriset P., Morken P. J., Org. Lett., 6, 2309-2312 (2004).
23. Zhao D., Oisaki K., Kanai M., Shibasaki M., J. Am. Chem. Soc., 128, 14440-14441 (2006).
24. Freiría M., Whitehead A. J., Tocher D. A., Motherwell W. B., Tetrahedron, 60, 2673-2692 (2004).
25. Lipshutz B. H., Amorelli B., Unger J. B., J. Am. Chem. Soc., 130, 14378-14379 (2008).
26. Burns A. R., Solana González J., Lam H. W., Angew. Chem. Int. Ed., 51, 10827-10831 (2012).
27. Ukaji Y., Shimizu Y., Kenmoku Y., Ahmed A., Inomata K., Chem. Lett., 26, 59-60 (1997).
28. Wei W., Kobayashi M., Ukaji Y., Inomata K., Chem. Lett., 35, 176-177 (2006).
29. Konishi A., Wei W., Kobayashi M., Fujinami S., Ukaji Y., Inomata K., Chem. Lett., 36, 44-45 (2007).