Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes
Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes
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DOI：
10.1002/anie.200501251
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发表时间：
2005-01-01
影响因子：
16.6
通讯作者：
Hoveyda, AH
中科院分区：
文献类型：
--
作者：
Brown, MK;Degrado, SJ;Hoveyda, AH
66 84 98 94 [a]在N2下进行反应。氧化步骤：PCC（吡啶氯铬酸盐；2.1当量），NaOAc, celite， 4-分子筛，CH2Cl2；产品a的浓度为0-60%；详细信息请参见支持信息。[b]> 98%的转化率，除了条目3 (65-70%)；通过分析未纯化产物的400 MHz 1H NMR谱来确定转化率。ACA/aldol加成步骤的分离产率；分离的氧化收率约为85%。[c]手性高效液相色谱法测定；详细信息请参见支持信息。[d]反应在À158C上进行。
66 84 98 94 [a] Reactions were carried out under N2. Oxidation step: PCC (pyridinium chlorochromate; 2.1 equiv), NaOAc, celite, 4-molecular sieves, CH2Cl2; products a are obtained in 0–60% de; see the Supporting Information for details.[b]> 98% conversion in all cases, except entry3 (65–70%); conversion determined by analysis of 400 MHz 1H NMR spectra of unpurified products. Isolated yields for the ACA/aldol addition step; isolated yields for oxidations are> 85%.[c] Determined by chiral HPLC analysis; see the Supporting Information for details.[d] Reaction was carried out at À158C.