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使用手性二胺衍生的硫脲催化剂对环状酸酐进行对映选择性硫解和氨解反应。

Enantioselective Thiolysis and Aminolysis of Cyclic Anhydrides Using a Chiral Diamine-Derived Thiourea Catalyst.

作者信息

Shim Jae Ho, Park Sung Joo, Ahn Byung Kook, Lee Ji Yeon, Kim Hyeon Soo, Ha Deok-Chan

机构信息

Department of Anatomy, Korea University College of Medicine, 46, Gaeunsa 2-gil, Seongbuk-gu, Seoul 02842, Republic of Korea.

Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Korea.

出版信息

ACS Omega. 2021 Nov 24;6(50):34501-34511. doi: 10.1021/acsomega.1c04741. eCollection 2021 Dec 21.

DOI:10.1021/acsomega.1c04741
PMID:34963935
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8697410/
Abstract

Catalytic desymmetrization of cyclic anhydrides has been widely investigated in the field of organocatalysis. Using this approach, many stereocenters can be established in a single, symmetry-breaking transformation. Herein, a thiourea organocatalyst was prepared in a single step from a chiral diamine, (,)-1,2-diphenylethylenediamine, and used for the desymmetrization of various cyclic anhydrides through double hydrogen-bonding activation. The asymmetric ring-opening reaction of the cyclic anhydride proceeded via the enantioselective addition reaction catalyzed by diamine thiourea. Thiolysis afforded the desired products in the yields of 86-98% and enantioselectivities of 60-94%, while aminolysis afforded the yields of 90-94% and enantioselectivities of 90-95%.

摘要

环状酸酐的催化去对称化在有机催化领域已得到广泛研究。通过这种方法，可以在单一的对称破缺转化中构建许多立体中心。在此，一种硫脲有机催化剂由手性二胺（，）-1,2-二苯基乙二胺一步制备而成，并用于通过双氢键活化实现各种环状酸酐的去对称化。环状酸酐的不对称开环反应通过二胺硫脲催化的对映选择性加成反应进行。硫解以86 - 98%的产率和60 - 94%的对映选择性得到所需产物，而氨解以90 - 94%的产率和90 - 95%的对映选择性得到所需产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/431321745129/ao1c04741_0014.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/431321745129/ao1c04741_0014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/898c88954ef2/ao1c04741_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/9176ead4d728/ao1c04741_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/496ab2449f12/ao1c04741_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/fdf1416cf902/ao1c04741_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/726c29804d39/ao1c04741_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/9bf3c5bf3ddc/ao1c04741_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/d323cc7b91bb/ao1c04741_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/7cd2e6867b87/ao1c04741_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/9c72464cc394/ao1c04741_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/318bbcfa2496/ao1c04741_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/e2e84907d994/ao1c04741_0013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/9fe25254c7d4/ao1c04741_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b39a/8697410/431321745129/ao1c04741_0014.jpg

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