手性有機(jī)銅（手性惡唑啉）催化劑催化下，端基炔和硝酮進(jìn)行偶極環(huán)加成得到異惡唑啉中間體，重排后得到立體選擇性的β-內(nèi)酰胺的反應(yīng)。
反應(yīng)機(jī)理
反應(yīng)實(shí)例
(3S, 4S)-1,3,4-Triphenyl-2-azetidinone (5). (S)-trisoxazoline 6 (11.3 mg, 0.03 mmol) and Cu(ClO4)2.H2O (9.3 mg, 0.025 mmol) in 4 mL MeCN were stirred for 2 h at 15 C. After cooling to 0 C, dicyclohexylamine (0.25 mmol) was added, followed after 10 min by phenylacetylene 1 (38 mg, 0.375 mmol). The color turned yellow and 0.25 mmol of nitrone 2 was added. The reaction was monitored by TLC and after 35 h the mixture was first filtered over silica gel using DCM as eluent and the solvent evaporated. Flash chromatography (PE/DCM) gave b-lactam 5 in 56% yield,[a]20 D ? 8.0 (c ?1.62, CHCl3) and 82%ee.
【Tang Y, J Org Chem, 2006, 71, 3576】
相關(guān)文獻(xiàn)
1 Kinugasa M J Chem Soc Chem Comm 1972 466
2 Fu GC J Am Chem Soc 2002 124 4572
3 Basak A Tet Lett 2002 43 5499
4* Fu GC Angew Chem Int 2003 42 4082
5 Marco-Contelles J Angew Chem Int 2004 43 2198
6* Tang Y J Org Chem 2006 71 3576
7* Guiry PJ Tet Asymm 2007 18 199
8 Basak A Synlett 2007 2321
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10 Hsung RP Org Lett 2008 10 3477
11* Saito T Tet Lett 2009 50 4969
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編譯自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 259.
相關(guān)反應(yīng)
Breckport β-內(nèi)酰胺合成
