Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning

Author:

Hamashima Yoshitaka,Kanai Motomu,Shibasaki Masakatsu

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference4 articles.

1. Catalytic Enantioselective Cyanosilylation of Ketones

2. For other examples using chemical catalyst, see; Belokon’, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Tararov, V. I. Tetrahedron Lett. 1999, 40, 8147–8150 and references cited therein.

3. Enantioselective Lewis acid–Lewis base bifunctional catalysts have been applied to a variety of reactions: Hamashima, Y.; Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 2641–2642; Kanai, M.; Hamashima, Y.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 2405–2409; Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2000, 39, 1650–1652; Takamura, M.; Funabashi, K.; Kanai, M. Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327–6328.

4. Spectroscopic data for 2-L: 1H NMR (500 MHz, CDCl3); δ 1.94 (m, 1H), 2.16 (m, 1H), 2.72 (ddd, J=9.45, 15.0, 15.0 Hz, 1H), 2.84 (ddd, J=3.35, 9.45, 15.3 Hz, 1H), 3.23 (m, 1H), 3.38 (ddd, J=3.05, 9.15, 16.5 Hz, 1H), 3.60 (ddd, J=5.20, 8.90, 11.3 Hz, 1H), 3.74 (dd, J=8.90, 9.20 Hz, 1H), 3.89 (m, 1H), 6.98 (d, J=8.25 Hz, 1H), 7.43–7.80 (m, 18H), 9.73 (s, 1H): 13C NMR (125.65 MHz, CDCl3); δ 31.5, 36.0 (d, J=68.2 Hz), 65.3, 74.7, 75.8, 84.8, 116.5, 123.8, 128.0, 128.7, 128.8, 128.8, 128.9, 129.0, 129.0, 129.6, 130.0, 130.5, 130.6, 130.8, 130.9, 131.0, 131.2, 131.7, 132.1, 132.3, 138.3, 145.7, 154.8, 195.1: 31P NMR (202.35 MHz, CDCl3); δ 34.5: [α]D27 +13.2 (c=2.34, CHCl3).

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