Functionalizing the γ-Position of α-Diazo-β-ketoesters.
Functionalizing the γ-Position of α-Diazo-β-ketoesters.
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DOI：
10.1016/j.tetlet.2016.06.065
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发表时间：
2016-06-27
影响因子：
1.8
通讯作者：
Buynak JD
中科院分区：
文献类型：
--
作者：
Nguyen TQ;Alqurafi M;Edwards C;Nguyen P;Kim J;Casco S;Bennet M;Chiang C;Lohry M;Cox M;Meshram B;Le D;Kim E;Smriti S;Oelschlaeger P;Buynak JD
虽然α-重氮-β-酮酯是一种合成用途广泛的中间体，但将这种功能引入复杂分子的方法仍然有限，最常见的是涉及羧酸前体，然后将其激活并转化为β-酮酯，随后用重氮转移试剂添加重氮基团。虽然在收敛的一步过程中引入这种高功能片段是理想的，但这一目标受到相对较少的研究的限制，这些研究涉及α-重氮-β-酮酯在γ-位置的功能化。在目前的研究中，我们评估了α-重氮-β-酮酯功能化的新策略和现有策略，特别是在合成c1取代碳青霉烯类化合物方面。本文报道了第一种δ-醛-α-重氮-β-酮酯及其在碱性条件下氧化生成相应甲酯和新取代吡唑的方法。
Although α-diazo-β-ketoesters are synthetically versatile intermediates, methodology for introducing this functionality into complex molecules is still limited, most frequently involving a carboxylic acid precursor, which is then activated and transformed into a β-ketoester, with the diazo group being subsequently added with a diazo transfer reagent. While introducing this highly functional moiety in a convergent one step process would be ideal, such an objective is limited by the relatively few studies which address functionalization of the α-diazo-β-ketoester at the γ-position. In the present investigation, we evaluate strategies, both new and established, for functionalizing α-diazo-β-ketoesters, particularly with regard to generating compounds prospectively useful in the synthesis of C1-substituted carbapenems. We report the first δ-aldehydo-α-diazo-β-ketoester as well as a method for its oxidation to the corresponding methyl ester, and the formation of a new substituted pyrazole under basic conditions.
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