トリス(トリメチルシリル)アルミニウムによるα-イミノエステルのジアステレオ選択的還元

SHIMIZU Makoto; NIWA Yasuki; NAGAI Takeshi; HACHIYA Iwao

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J-GLOBAL ID：200902261011297722 整理番号：07A0419785

トリス(トリメチルシリル)アルミニウムによるα-イミノエステルのジアステレオ選択的還元

DIASTEREOSELECTIVE REDUCTION OF α-IMINO ESTERS WITH TRIS(TRIMETHYLSILYL)ALUMINUM

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著者 (4件)： , , ,
資料名：
巻： 72 ページ： 127-132 発行年： 2007年04月13日
JST資料番号： S0966A ISSN： 0385-5414 CODEN： HTCYAM 資料種別：逐次刊行物 (A)
記事区分：短報発行国：日本 (JPN) 言語：英語 (EN)

トリス(トリメチルシリル)アルミニウムはα-アミノエステルを...

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芳香族単環カルボン酸エステル・カルボン酸無水物・酸ハロゲン化物 , 酸化,還元

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引用文献 (5件)：

(a) G. G. Cox and L. M. Harwood, Tetrahedron: Asymmetry, 1994, 5, 1669.(b) F. Seggat-Dioury, O. Lingibe, B. Graffe, M.-C. Sacquet, and G. Lhommet, Tetrahedron, 2000, 56, 233.
(a) M. P. Bertrand, L. Feray, R. Nouguier, and P. Perfetti, Synlett, 1999, 1148.(b) K. Uneyama, F. Yan, S. Hirama, and T. Katagiri, Tetrahedron Lett., 1996, 37, 2045.(c) Y. Yamamoto and W. Ito, Tetrahedron, 1988, 44, 5415.(d) M. R. van Vliet, J. T. B. H. Jastrzebski, W. J. Klaver, K. Goubitz, and G. van Koten, Recl. Trav. Chim. Pays-Bas, 1987, 106, 132.(e) J.-C. Fiaud and H. B. Kagan, Tetrahedron Lett., 1971, 12, 1019.
(a) Y. Niwa and M. Shimizu, J. Am. Chem. Soc., 2003, 125, 3720.(b) M. Shimizu and Y. Niwa, Tetrahedron Lett., 2001, 42, 2829.(c) Y. Niwa, K. Takayama, and M. Shimizu, Bull. Chem. Soc. Jpn., 2002, 75, 1819.(d) Y. Niwa, K. Takayama, and M. Shimizu, Tetrahedron Lett., 2001, 42, 5473.(e) M. Shimizu, H. Itou, and M. Miura, J. Am. Chem. Soc., 2005, 127, 3296.
(a) M. A. Avery, W. K. M. Chong, and C. Jennings-White, J. Am. Chem. Soc., 1992, 114, 974.(b) M. Nakada, S. Nakamura, S. Kobayashi, and M. Ohno, Tetrahedron Lett., 1991, 32, 4929.(c) G. Altnau and L. Rösch, Tetrahedron Lett., 1983, 24, 45.(d) B. M. Trost, J. Yoshida, and M. Lautens, J. Am. Chem. Soc., 1983, 105, 4494.(e) L. Rösch and G. Altnau, J. Organomet., Chem., 1980, 195, 47.
The following example represents typical experimental procedure: To a solution of (5S)-5-isopropyl 3-phenyl-5, 6-dihyro-2H-1, 4-oxazine-2-one (32.6 mg, 0.150 mmol)(5) in DME (1.5 mL) was added a solution of BF₃OEt₂ (21.3 mg, 0.150 mmol) in DME (1.5 ml) at-60°C under an argon atmosphere. To the resulting solution was added a solution of tris (trimethylsilyl) aluminum (6)(0.300 mL, 0.150 mmol, 0.5 M in pentane) at-60°C. The mixture was allowed to warm to ambient temperature with stirring for 8.0 h. The reaction was cooled to-60°C and quenched with MeOH (0.122 mL, 3.00 mmol). To the resulting solution was added sat. NaHCO₃ aq, and the whole mixture was extracted with AcOEt. The combined organic layers were washed with brine, dried over anhydrous Na₂SO₄, and concentrated in vacuo. Purification by flash silica gel column (n-hexane-AcOEt=4:1 as an eluent) gave 5-isopropyl-3-phenylmorpholine-2-one (5)(17.8 mg, 54%, a 92:8 mixture of cis and trans isomers) as a colourless oil; ¹H NMR (500 MHz, CDCl₃) δ: 0.98 (d, J=7.3 Hz, 3H), 1.02 (d, J=6.7 Hz, 3H), 1.71-1.75 (m, 1H), 1.92 (brs, 1H), 2.83-2.89 (m, 0.08H), 2.99-3.04 (m, 0.92H), 4.23-4.27 (m, 1H), 4.40-4.45 (m, 1H), 4.72 (s, 0.92H), 4.86 (s, 0.08H), 7.33-7.50 (m, 5H); ¹³C NMR (126 MHz, CDCl₃) δ: 18.7, 18.9, 30.2, 58.0, 63.6, 72.8, 127.2, 128.3, 128.6, 138.4, 169.2; IR (neat) 3329, 3031, 2963, 1739, 1460, 1369, 1294, 1205, 1092, 1028, 968, 867, 743, 700 cm^-1.

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