Absolute Asymmetric Synthesis of Tertiary a-Amino Acids

被引：21

作者：

Thi Thoa Mai ^{[1
]}

Branca, Mathieu ^{[1
]}

Gori, Didier ^{[1
]}

Guillot, Regis ^{[1
]}

Kouklovsky, Cyrille ^{[1
]}

Alezra, Valerie ^{[1
]}

机构：

[1] Univ Paris 11, Lab Chim Procedes & Subst Nat, CNRS, ICMMO,UMR 8182, F-91405 Orsay, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 20期

关键词：

amino acids; amides; asymmetric synthesis; chirality; synthetic methods; ENANTIOSELECTIVE SYNTHESIS; CHIRAL CRYSTALLIZATION; MOLECULAR CHIRALITY; OPTICAL-ACTIVITY; AROMATIC AMIDES; MEMORY; HOMOLOGATION; GENERATION; ROTATION; ACCESS;

D O I：

10.1002/anie.201200950

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Frozen: The spontaneous crystallization of an achiral compound in a chiral conformation is used as the unique source of chirality in an absolute asymmetric synthesis of tertiary amino acids. The dynamic axial chirality of tertiary aromatic amides is frozen in a crystal (see picture) and is responsible for the stereoselectivity of the deprotonation/alkylation (see scheme). α-Amino acid derivatives are synthesized in up to 96% ee. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4981 / 4984

页数：4

共 50 条

[31] Practical Asymmetric Synthesis of Fluorinated Amino Acids and Their Application to Peptide Engineering
Ishida, Yasuhiro
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (07) : 703 - 712
[32] Catalytic asymmetric alkylation of nucleophiles:: Asymmetric synthesis of α-alkylated amino acids
Trost, BM
Ariza, X
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2635 - 2637
[33] An Organocatalytic Asymmetric Synthesis of Chiral β,β-Diaryl-α-amino Acids via Addition of Azlactones to In Situ Generated para-Quinone Methides
Yan, Jiyao
Chen, Min
Sung, Herman H-Y.
Williams, Ian D.
Sun, Jianwei
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2440 - 2444
[34] Asymmetric synthesis of substituted azetidine type α- and β-amino acids
Enders, D
Gries, J
SYNTHESIS-STUTTGART, 2005, Georg Thieme Verlag (20): : 3508 - 3516
[35] Photochirogenesis: Photochemical models on the absolute asymmetric formation of amino acids in interstellar space
Meinert, Cornelia
de Marcellus, Pierre
d'Hendecourt, Louis Le Sergeant
Nahon, Laurent
Jones, Nykola C.
Hoffmann, Soren V.
Bredehoeft, Jan Hendrik
Meierhenrich, Uwe J.
PHYSICS OF LIFE REVIEWS, 2011, 8 (03) : 307 - 330
[36] New Progress in Asymmetric Synthesis of Quaternary α-Amino Acids
Jiang, Han
Jin, Yi
Lin, Jun
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2017, 14 (06) : 434 - 447
[37] Asymmetric Synthesis of Quaternary α-Amino Acids and Their Phosphonate Analogues
Bera, Kalisankar
Namboothiri, Irishi N. N.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (12) : 1234 - 1260
[38] Synthesis and Photophysical Properties of Charge-Transfer-Based Pyrimidine-Derived a-Amino Acids
Songsri, Sineenard
Harkiss, Alexander H.
Sutherland, Andrew
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (18): : 13214 - 13224
[39] Asymmetric Synthesis of Perfluoroalkylated α-Amino Acids through Generated Radicals Using a Chiral Ni(II) Complex
Stoletova, Nadezhda, V
Moshchenkov, Andrey D.
Smol'yakov, Alexander F.
Gugkaeva, Zalina T.
Maleev, Victor, I
Katayev, Dmitry
Larionov, Vladimir A.
HELVETICA CHIMICA ACTA, 2021, 104 (01)
[40] Adding a Functional Handle to Nature's Building Blocks: The Asymmetric Synthesis of β-Hydroxy-α-Amino Acids
Zhang, Yinfeng
Farrants, Helen
Li, Xuechen
CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (07) : 1752 - 1764

← 1 2 3 4 5 →