An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: Serendipity rules

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2133-2136

  Nugent, William A ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINOALCOHOL; LIGAND; MORPHOLINE; MORPHOLINE DERIVATIVE; ORGANOMETALLIC COMPOUND; ZINC;

ARTICLE; CHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALDEHYDES; AMINO ALCOHOLS; LIGANDS; MORPHOLINES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; ZINC;

EID: 0037182689     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0259488     Document Type: Article

References (21)

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13. For assignments see, the following. (R)-(+)-1-Phenyl-1-propyl acetate: Faraldos, J.; Arroyo, E.; Herradon, B. Synlett 1997, 367. (R)-(+)-3-Octyl acetate: Mihailovic, M. Lj.; Mamuzic, R. I.; Zigic-Mamuzic, Lj.; Bosnjak, J.; Cekovic, Z. Tetrahedron 1967, 23, 215, (S)-(-)-1-Cyclohexyl-1-propyl acetate: Levene, P. A.; Marker, R. E. J. Biol. Chem. 1932, 97, 379.
14. For assignments see, the following. (R)-(+)-1-Phenyl-1-propyl acetate: Faraldos, J.; Arroyo, E.; Herradon, B. Synlett 1997, 367. (R)-(+)-3-Octyl acetate: Mihailovic, M. Lj.; Mamuzic, R. I.; Zigic-Mamuzic, Lj.; Bosnjak, J.; Cekovic, Z. Tetrahedron 1967, 23, 215, (S)-(-)-1-Cyclohexyl-1-propyl acetate: Levene, P. A.; Marker, R. E. J. Biol. Chem. 1932, 97, 379.
15. For assignments see, the following. (R)-(+)-1-Phenyl-1-propyl acetate: Faraldos, J.; Arroyo, E.; Herradon, B. Synlett 1997, 367. (R)-(+)-3-Octyl acetate: Mihailovic, M. Lj.; Mamuzic, R. I.; Zigic-Mamuzic, Lj.; Bosnjak, J.; Cekovic, Z. Tetrahedron 1967, 23, 215, (S)-(-)-1-Cyclohexyl-1-propyl acetate: Levene, P. A.; Marker, R. E. J. Biol. Chem. 1932, 97, 379.
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17. Although addition of morpholine to trans-stilbene oxide was rather slow at 90°C in our initial studies, a subsequent report by Pericas suggests that this addition may be greatly accelerated in the presence of lithium perchlorate. We have not yet tested this possibility. Sola, L.; Reddy, K. S.; Vidal-Ferran, A.; Moyano, A.; Pericas, M. A.; Rieras, A.; Alvarez-Larena, A.; Piniella, J.-F. J. Org. Chem. 1998, 63, 7078.
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19. See, for example: Chang, H.-T.; Sharpless, K. B. J. Org. Chem. 1996, 61, 6456. Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
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