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用于各种酮与醛的无溶剂不对称羟醛反应的新型小γ-转角型-伯氨基末端三肽有机催化剂。

New small γ-turn type -primary amino terminal tripeptide organocatalyst for solvent-free asymmetric aldol reaction of various ketones with aldehydes.

作者信息

Thiyagarajan Rajkumar, Begum Zubeda, Seki Chigusa, Okuyama Yuko, Kwon Eunsang, Uwai Koji, Tokiwa Michio, Tokiwa Suguru, Takeshita Mitsuhiro, Nakano Hiroto

机构信息

Division of Sustainable and Environmental Engineering, Graduate School of Engineering, Muroran Institute of Technology 27-1 Mizumoto-cho Muroran 050-8585 Japan

Tohoku Medical and Pharmaceutical University 4-4-1 Komatsushima Aoba-Ku Sendai 981-8558 Japan.

出版信息

RSC Adv. 2021 Dec 6;11(61):38925-38932. doi: 10.1039/d1ra08635a. eCollection 2021 Nov 29.

DOI:10.1039/d1ra08635a
PMID:35493209
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9044195/
Abstract

New small γ-turn type -primary amino terminal tripeptides were synthesized and their functionality as an organocatalyst was examined in the asymmetric aldol reaction of various ketones with different aromatic aldehydes under solvent-free neat conditions to afford the desired chiral -aldol products in good to excellent chemical yields, diastereoselectivities and enantioselectivities (up to 99%, up to  : /13 : 87 dr, up to 99% ee).

摘要

合成了新型小γ-转角型-一级氨基末端三肽，并在无溶剂纯条件下，考察了它们作为有机催化剂在各种酮与不同芳香醛的不对称羟醛反应中的功能，以良好至优异的化学产率、非对映选择性和对映选择性（高达99%，高达13:87的非对映体比例，高达99%的对映体过量）得到所需的手性羟醛产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/5047cdedc199/d1ra08635a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/08b5cf70328a/d1ra08635a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/31c387ef0fb7/d1ra08635a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/4bce6f55a1bb/d1ra08635a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/9c0c158c2466/d1ra08635a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/c5347a3fee2e/d1ra08635a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/5047cdedc199/d1ra08635a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/08b5cf70328a/d1ra08635a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/31c387ef0fb7/d1ra08635a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/4bce6f55a1bb/d1ra08635a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/9c0c158c2466/d1ra08635a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/c5347a3fee2e/d1ra08635a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55bb/9044195/5047cdedc199/d1ra08635a-f1.jpg

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