Asymmetric carbonyl addition reactions to benzyloxyaldehydes by binaphthol-titanium catalyst: Anti- vs. syn-diastereofacial preference in anomalous nonchelation complexation

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1951-1954

  Mikami, Koichi ^b   Matsukawa, Satoru ^b   Sawa, Eiji ^b   Harada, Akinori ^a   Koga, Nobuaki ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; HYDROXYALDEHYDE;

ARTICLE; CHELATION; CHEMICAL REACTION; COMPLEX FORMATION; DIASTEREOISOMER; DRUG SYNTHESIS;

EID: 0031575791     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00231-1     Document Type: Article

References (41)

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15. 4 The reaction was carried out by adding the olefin or the trimethylsilyl enol ether and the benzyloxy aldehydes 3 at 0 °C to a dichloromethane or toluene solution containing 10 to 20 mol% of the chiral titanium catalyst 1, prepared as previously reported: Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940-1941; 1990, 112, 3949-3954; Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1993, 77, 14-21.
16. 4 The reaction was carried out by adding the olefin or the trimethylsilyl enol ether and the benzyloxy aldehydes 3 at 0 °C to a dichloromethane or toluene solution containing 10 to 20 mol% of the chiral titanium catalyst 1, prepared as previously reported: Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940-1941; 1990, 112, 3949-3954; Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1993, 77, 14-21.
17. 4 The reaction was carried out by adding the olefin or the trimethylsilyl enol ether and the benzyloxy aldehydes 3 at 0 °C to a dichloromethane or toluene solution containing 10 to 20 mol% of the chiral titanium catalyst 1, prepared as previously reported: Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940-1941; 1990, 112, 3949-3954; Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Org. Synth. 1993, 77, 14-21.
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31. 9 Syn-stereochemistry of aldol product 8 was determined after conversion to the cis-pentanolide, of which the authentic sample was obtained via hydrogenolysis and lactonization of syn-4d.
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33. 11 Exactly the same sense of enantiofacial selectivity has been observed in carbonyl-ene and aldol reactions with prochiral benzyloxyacetoaldehyde: High (>85% ee) levels of (2R)-enantiofacial selectivity are obtained with (R)-BINOL-Ti catalyst 1 in both ene and aldol reactions.
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41. 15 There may be partial involvement of chelation complexation in the syn-selective aldol reaction of (S)-benzyloxy aldehyde (3) catalyzed by (S)-1.