ASYMMETRIC INTRAMOLECULAR ALDOL REACTIONS MEDIATED BY CHIRAL TRIAMINES BEARING A PYRROLIDINE SCAFFOLD TO PROVIDE A WIELAND-MIESCHER KETONE

被引：0

作者：

Akahane, Yuichi ^{[2
]}

Inomata, Kohei ^{[1
,2
]}

机构：

[1] Int Univ Hlth & Welf, Dept Pharmaceut Sci, 2600-1 Kitakanemaru, Ohtawara 3248501, Japan

[2] Tohoku Med & Pharmaceut Univ, Dept Pharm, Aoba Ku, 4-4-1 Komatsushima, Sendai, Miyagi 9818558, Japan

来源：

HETEROCYCLES | 2022年 / 105卷 / 01期

关键词：

BIFUNCTIONAL ORGANOCATALYSTS; TRANSITION-STATES; MICHAEL ADDITION; AMINO-ACID; PROLINE; STEREOSELECTIVITY; PROLINAMIDES; PREDICTIONS; DERIVATIVES; CATALYSTS;

D O I：

10.3987/COM-22-S(R)12

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We established a new asymmetric route to provide (R)-Wieland- Miescher ketone [(R)-2] using a combination of trifluoroacetic acid (TFA) and known or new chiral triamines (7) bearing a pyrrolidine scaffold. Although the intramolecular aldol reaction of trione (1) mediated by chiral prrolidine (7) resulted in the production of 2 with low enantioselectivities, a remarkably increased enantioselectivity with a combination of 7b or 7c and TFA was observed. We also found that a secondary amine motif existing in the middle of the side chain was important in defining the enantioselectivity.

引用

页码：566 / 575

页数：10

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