Diastereoselective formation of cyanohydrins from α-alkoxy aldehydes

Organic Letters

Volumn 2, Issue 1, 2000, Pages 57-60

  Ward, Dale E ^a   Hrapchak, Matthew J ^a   Sales, Marcelo ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

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[No Author keywords available]

Indexed keywords

EID: 0002323853     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991198z     Document Type: Article

References (52)

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36. Enantiotopic group selectivity (E) can be estimated from the following equation where r is the reagent-controlled selectivity (i.e., enantioselectivity from achiral substrate with chiral reagent) and s is the substrate-controlled selectivity (i.e., the diastereoselectivity from chiral substrate with achiral reagent): E = (rs + 1)/(r + s). For a discussion, see ref 7a.
37. 2(TADDOL)/TMSCN: (a) Narasaka, K.; Minamikawa, H.; Hayakawa, S.; Yamada, T.; Iwasawa, N. Bull. Chem. Soc. Jpn. 1988, 61, 4379.
38. 2(BINOL)/TMSCN:
39. Mori, M.; Imma, H.; Nakai, T. Tetrahedron Lett. 1997, 38, 6229.
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41. Ca. 8.5 mg/mL (0.033 M) at ambient temperature.
42. 4NCN failed to give 2a.
43. 12 or affect the diastereomer distribution.
44. 2O, pyridine; ca. 30% overall yield) to the known threitol tetraacetate (Vogel, P.; Jeganathan, S. J. Org. Chem. 1991, 56, 1133); 2b by analogy.
45. 3: C, 41.40; H, 7.96; N, 14.48; Ag, 37.17. Found: C 41.59; H, 7.34; N, 13.98; Ag, 36 (by precipitation of AgCl).
46. -12) (Handbook of Analytical Chemistry; Meites, L., Ed.; McGraw-Hill: New York, 1963; Section 1, p 13), and the empirical formula is consistent with the elemental analysis (note 15).
47. This increase is consistent with a simple temperature effect [i.e., dr at 195 K = (dr at 273 K) exp(273/195)].
48. 2 but were not reproducible and often were interior.
49. 2 (5 equiv) at 0°C for 1 h gave a 3:1:2 mixture of 2d (5:1, syn/anti), 2a, and the TMS ether of 2a (1.3: 1, syn/anti), respectively.
50. 2 gave 2e with attenuated selectivity.
51. 2 can add to 1 (Table 3, entry 7).
52. For an example of high syn selectivity from a nonchelated complex, see: Mikami, K.; Matsukawa, S.; Sawa, E.; Harada, A.; Koga, N. Tetrahedron Lett. 1997, 38, 1951.