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Enantioselective vinylogous aldol reaction of acylphosphonates with 3-alkylidene oxindoles
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-08-13 , DOI: 10.1039/d1ob00140j Manish K Jaiswal 1 , Sanjay Singh 1 , Ravi P Singh 1
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-08-13 , DOI: 10.1039/d1ob00140j Manish K Jaiswal 1 , Sanjay Singh 1 , Ravi P Singh 1
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A simple strategy for yielding chiral tertiary α-hydroxy phosphonates that integrates two highly biologically relevant scaffolds namely 3-alkylidene-2-oxindoles and phosphonates has been described. The hydrogen bonding ability of the bifunctional thiourea catalyst allows simultaneous dual activation of a vinylogous oxindole nucleophile and an acylphosphonate electrophile, affording hydroxyphosphonato-3-alkylidene-2-oxindoles as aldol adducts in high yields (up to 92%) with excellent stereocontrol (up to 99% ee).
中文翻译：
酰基膦酸酯与 3-亚烷基羟吲哚的对映选择性乙烯醇醛醇反应
已经描述了一种用于产生手性叔 α-羟基膦酸盐的简单策略，该策略集成了两个高度生物学相关的支架，即 3-亚烷基-2-羟吲哚和膦酸盐。双功能硫脲催化剂的氢键结合能力允许同时双重活化乙烯基羟吲哚亲核试剂和酰基膦酸酯亲电试剂，以高产率（高达 92%）和优异的立体控制（高达至 99% ee)。
更新日期：2021-09-03
中文翻译：
酰基膦酸酯与 3-亚烷基羟吲哚的对映选择性乙烯醇醛醇反应
已经描述了一种用于产生手性叔 α-羟基膦酸盐的简单策略，该策略集成了两个高度生物学相关的支架，即 3-亚烷基-2-羟吲哚和膦酸盐。双功能硫脲催化剂的氢键结合能力允许同时双重活化乙烯基羟吲哚亲核试剂和酰基膦酸酯亲电试剂，以高产率（高达 92%）和优异的立体控制（高达至 99% ee)。
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