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Enantioselective Catalytic Boronate Reactions

对映选择性催化硼酸酯反应

基本信息

批准号：
9402611
负责人：
Scott Edward Schaus
金额：
$ 37.98万
依托单位：
BOSTON UNIVERSITY (CHARLES RIVER CAMPUS)
依托单位国家：
美国
项目类别：
财政年份：
2007
资助国家：
美国
起止时间：
2007-04-01 至 2019-12-31
项目状态：
已结题

项目摘要

DESCRIPTION (provided by applicant): The development of new chemical methodologies is an important objective of organic synthesis. An area that continues to inspire chemists is the chemistry of organoboranes and boronates. The unique properties of boron and the ability to activate organic boronates to deliver carbon nucleophiles has yielded an impressive array of chemical methods and processes. We will extend the ability of organoboranes and boronates to deliver carbanion equivalents in novel condensation reactions including chemoselective carbonyl condensations and multicomponent reactions. The reactions will be rendered asymmetric through the development of asymmetric catalysts and chiral boronate reagents and the utility of the methods developed demonstrated by the asymmetric synthesis of pharmaceuticals and natural products. Significant advances have been made in the mechanistic understanding of boronate activation via ligand exchange with chiral diols. We will use the mechanistic insight we have obtained to expand the repertoire of reactions catalyzed by dynamic ligand exchange processes to include acyl cyanides as electrophiles, borono-Petasis reactions, and ortho-quinone methide chemistry. Our continued interest in reaction discovery has led to the identification of chiral diol acid catalysts capable of promoting the enantioselectie addition reactions to acetals. We seek to explore this reactivity and expand it to include types of functionalized nucleophiles in additions to oxoniums and iminiums and boronate hetero-Diels-Alder reactions. Goals of the research program include developing a breadth of reactivity, providing access to novel chiral blocks, and new reaction development. Bond constructions are selected to access chiral synthetic intermediates that could be used in the construction of pharmaceuticals and natural products. The results will transform the way boronate nucleophiles are utilized in enantioselective synthesis.

描述（由申请人提供）：开发新的化学方法是有机合成的一个重要目标。有机硼烷和硼酸盐的化学是一个继续激发化学家灵感的领域。硼的独特性质和活化有机硼酸盐以提供碳亲核试剂的能力已经产生了一系列令人印象深刻的化学方法和工艺。我们将扩展有机硼烷和硼酸盐在新型缩合反应中提供碳负离子当量的能力，包括化学选择性羰基缩合和多组分反应。通过开发不对称催化剂和手性硼酸酯试剂，以及通过药物和天然产物的不对称合成证明的所开发方法的实用性，将使反应变得不对称。通过与手性二醇的配体交换，硼酸酯活化的机理理解已经取得了重大进展。我们将使用我们已经获得的机制的见解，以扩大由动态配体交换过程催化的反应，包括作为亲电体，borono-Petasis反应，和邻醌甲基化物化学的酰基氰化物的剧目。我们对反应发现的持续兴趣导致了能够促进缩醛的对映选择性加成反应的手性二元酸催化剂的鉴定。我们试图探索这种反应性，并将其扩展到包括以下类型：官能化的亲核试剂以及氧鎓和亚胺和硼酸化杂-Diels-桤木反应。该研究计划的目标包括开发广泛的反应性，提供新的手性嵌段和新的反应开发。选择键结构以获得可用于构建药物和天然产物的手性合成中间体。这些结果将改变硼酸酯亲核试剂在对映选择性合成中的应用。

项目成果

期刊论文数量（18）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

Enantioselective boronate additions to N-acyl quinoliniums catalyzed by tartaric acid.

用tart酸催化的N-酰基喹啉添加对映选择性富有硼酸盐。

DOI：
10.1021/ol2028702
发表时间：
2011-12-02
期刊：
Organic letters
影响因子：
5.2
作者：
Kodama T;Moquist PN;Schaus SE
通讯作者：
Schaus SE

Expansile Nanoparticles Encapsulate Factor Quinolinone Inhibitor 1 and Accumulate in Murine Liver upon Intravenous Administration.

可膨胀纳米颗粒封装因子喹啉酮抑制剂 1 并在静脉注射后在小鼠肝脏中积聚。

DOI：
10.1021/acs.biomac.0c00064
发表时间：
2020
期刊：
Biomacromolecules
影响因子：
6.2
作者：
Stoiber,Patrick;Ekladious,Iriny;Zhao,Qing;Colson,YolondaL;Schaus,ScottE;Hansen,Ulla;Grinstaff,MarkW
通讯作者：
Grinstaff,MarkW

Two naturally occurring mutations in the type 1 melanin-concentrating hormone receptor abolish agonist-induced signaling.

1 型黑色素浓缩激素受体中的两个自然发生的突变消除了激动剂诱导的信号传导。

DOI：
10.1124/jpet.110.174029
发表时间：
2010
期刊：
The Journal of pharmacology and experimental therapeutics
影响因子：
0
作者：
Goldstein,Carmit;Schroeder,JonathanC;Fortin,Jean-Philippe;Goss,JenniferM;Schaus,ScottE;Beinborn,Martin;Kopin,AlanS
通讯作者：
Kopin,AlanS

Factor quinolinone inhibitors alter cell morphology and motility by destabilizing interphase microtubules.