syn-selective direct catalytic asymmetric Mannich-type reactions of hydroxyketones using Y{N(SiMe3)2}3/linked-BINOL complexes

Organic Letters

Volumn 7, Issue 23, 2005, Pages 5339-5342

  Sugita, Mari ^a   Yamaguchi, Akitake ^a   Yamagiwa, Noriyuki ^a   Handa, Shinya ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244460830     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052384+     Document Type: Article

References (56)

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36. 2Zn/linked-BINOL 1a complex, see the following. Aldol reaction: (a) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
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43. Use of diphenylphosphinoyl imine is favorable because removal of the protective group is relatively easy. For a review for the use of diphenylphosphinoyl imines 2 in organic synthesis, see: Weinreb, S. M.; Orr, R. K. Synthesis 2005, 1205.
44. For highly enantioselective catalytic Mannich-type reactions using alkenyl imines, see the following. With enol silane and ketene silyl acetal as donors: (a) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734.
45. (b) Josephsohn, N. S.; Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Org. Lett. 2005, 7, 2711 and references therein. For direct Mannich-type reaction of alkenyl imines with 2-hydroxy-N-acylpyrrole as a donor, see ref 11.
46. 2Zn/linked-BINOL 1a complex (5 mol % of 1a), Mannich adducts were obtained in 58% ee with 2-hydroxyacetophenone 3b and in 36% ee with 2-hydroxyacetylfuran 3f. See ref 9b.
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49. For the determination of the relative and absolute configuration of Mannich adducts, see Supporting Information.
50. 3 compounds were purchased from Aldrich.
51. 3/linked-BINOL 1 complexes; see ref 11. Synthetic procedure of TMS-linked-BINOL 1b is also reported in ref 11.
52. 3/linked-BINOL 1a complexes showed only very broad peaks, suggesting complicated mixtures of oligomeric species. ESI-MS analysis also gave no useful information.
53. For use of 2-furyl group as a 4-oxygenated-2-enoic acid synthon using mild oxidation conditions (NBS, pyridine), see: (a) Kobayashi, Y.; Nakano, M.; Kumar, G. B.; Kishihara, K. J. Org. Chem. 1998, 63, 7505.
54. For use of 2-furyl group as an ester synthon, see also: (b) Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T. J. Org. Chem. 1997, 62, 5497.
55. (c) Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513 and references therein.
56. 2Zn/linked-BINOL 1a, α,β-unsaturated imine, and hydroxyketone 3a (with dpp-imine 2f, syn/anti = 19/81, 99% ee; with Boc-imine derived from cinnam aldehyde, syn/anti = 63/37, 99% ee): see ref 9b. Although ee was excellent, diastereoselectivity was only modest.