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Enantioselective Organocatalytic Synthesis of δ‐Lactone‐Fused 4‐Chromanones
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-08-04 , DOI: 10.1002/adsc.202000667
Yu‐Ting Lai, Koppanathi Nagaraju, Ramani Gurubrahamam, Kwunmin Chen

An organocatalytic enantioselective synthesis of δ‐lactone‐fused 4‐chromanones was demonstrated using 1‐(2‐hydroxyaryl)‐1,3‐butanedione and α,β‐unsaturated aldehydes in the presence of the Jørgensen‐Hayashi catalyst. The reaction proceeded through a Michael addition/cycloketalization/hemiacetalization sequence, and the resulting hemiacetals were oxidized into the corresponding lactone derivatives in a one‐pot manner. The desired fused O,O‐ketal tricyclic lactone motifs containing three contiguous chiral centers were obtained in excellent chemical yields (up to 97%) and with high stereoselectivities (up to >20:1 dr and up to 95% ee).

中文翻译:

对映体有机催化合成δ-内酯融合的4-色曼酮

在Jørgensen-Hayashi催化剂的存在下,使用1-(2-羟基芳基)-1,3-丁二酮和α,β-不饱和醛证明了δ-内酯融合的4-苯并二氢醌的有机催化对映选择性合成。反应按照迈克尔加成/环缩酮化/半缩醛化顺序进行,然后将生成的半缩醛以单锅方式氧化为相应的内酯衍生物。所需的包含三个连续手性中心的稠合的O,O-缩酮三环内酯基序以优异的化学收率(高达97%)和高的立体选择性(高达> 20:1 dr和高达95%ee)获得。
更新日期:2020-09-21
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