Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts

Guangning Ma; Shuangzheng Lin; Ismail Ibrahem

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Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts

机译：外消旋混合物（RRM）催化不对称反应中的非手性助催化剂诱导的转换：从氢键给体和手性胺催化剂的结合，从立体发散的RRM到立体收敛的脱气

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A stereochemical divergent approach for the highly enantioselective synthesis of distinct bicy-clic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine-catalyzed cascade reactions between racemic γ-nitro ketones and α,β-un-saturated aldehydes using different achiral co-catalysts. The utility of the method is exemplified by the highly diasteroselective switch and stereoconvergent deracemization process by combination of chiral amine and achiral hydrogen-bond-donating catalysts.

机译：公开了一种立体化学发散方法，其使用单一手性催化剂从外消旋物高度对映选择性地合成具有多个立构中心的独特的双环化合物。它基于使用不同的非手性助催化剂，在外消旋γ-硝基酮与α，β-不饱和醛之间进行手性胺催化的级联反应中整个反应路径的转换。该方法的实用性是通过手性胺和非手性氢键给体催化剂的结合进行的非对映选择性高的转换和立体收敛的脱硝过程来举例说明的。

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《Advanced synthesis & catalysis》 |2012年第15期|共8页
作者
Guangning Ma; Shuangzheng Lin; Ismail Ibrahem;
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正文语种 eng
中图分类化学工业;
关键词
cascade reactions; deracemization; dynamic asymmetric catalysis; hydrogen-bond donor; organocatalysis; reactions on racemic mixtures; stereodivergence;

机译：级联反应;脱硝作用;动态不对称催化;氢键供体;有机催化;外消旋混合物的反应;立体发散;

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专利

1. Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts [J] . Guangning Ma, Shuangzheng Lin, Ismail Ibrahem Advanced synthesis & catalysis . 2012,第14a15期

机译：外消旋混合物（RRM）催化不对称反应中的非手性助催化剂诱导的转换：从氢键给体和手性胺催化剂的结合，从立体发散的RRM到立体收敛的脱气
2. Stereoselective Reactions. Part 31:~1 Catalytic Asymmetric Alkylation of Achiral Lithium Enolates using a Chiral Tetradentate Amine in the Presence of an Achiral Bidentate Amine [J] . Imai Mitsuko Tetrahedron . 2000,第2期

机译：立体选择性反应。第31部分：〜1手性四齿胺存在下使用手性四齿胺催化手性锂烯醇盐的不对称烷基化
3. Highly Enantioselective Co-Catalytic Direct Aldol Reactions by Combination of Hydrogen-Bond Donating and Acyclic Amino Acid Catalysts [J] . Guangning Ma, Agnieszka Bartoszewicz, Ismail Ibrahem Advanced synthesis & catalysis . 2011,第17期

机译：氢键给体与无环氨基酸催化结合的高对映选择性共催化直接羟醛反应
4. Organocatalytic asymmetric Henry reaction of 1H-pyrrole-23-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors [O] . Ming-Liang Zhang, Deng-Feng Yue, Zhen-Hua Wang, 2016

机译：1H-吡咯-23-二酮与带有多个氢键供体的双官能胺-硫脲催化剂的有机催化不对称亨利反应
5. Corrigendum: Highly Enantioselective Co-Catalytic Direct Aldol Reactions by Combination of Hydrogen-Bond Donating and Acyclic Amino Acid Catalysts [O] . Guangning Ma, Agnieszka Bartoszewicz, Ismail Ibrahem, 2012

机译：勘误：通过组合氢键合和无循环氨基酸催化剂，高映选择性辅助醛醇反应

Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts

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