Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)-amino]acetyl}amino) benzophenone; a case of configurationally stable stereogenic nitrogen

被引：10

作者：

Moriwaki, Hiroki ^{[1
,2
]}

Resch, Daniel ^{[1
]}

Li, Hengguang ^{[1
]}

Ojima, Iwao ^{[1
]}

Takeda, Ryosuke ^{[2
]}

Luis Acena, Jose ^{[3
]}

Soloshonok, Vadim A. ^{[3
,4
]}

机构：

[1] SUNY Stony Brook, Dept Chem, Inst Chem Biol & Drug Discovery, Stony Brook, NY 11794 USA

[2] Hamari Chem Ltd, Higashi Yodogawa Ku, Osaka 5330024, Japan

[3] Univ Basque Country, Fac Chem, Dept Organ Chem 1, San Sebastian 20018, Spain

[4] Basque Fdn Sci, IKERBASQUE, Bilbao 48011, Spain

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷

基金：

美国国家科学基金会;

关键词：

amino acids; asymmetric synthesis; Ni(II) complexes; Schiff bases; stereogenic nitrogen; ALPHA-AMINO-ACIDS; MICHAEL ADDITION-REACTIONS; EFFICIENT ASYMMETRIC-SYNTHESIS; SUBSTITUTED PYROGLUTAMIC ACIDS; VIRTUALLY COMPLETE CONTROL; PHASE-TRANSFER CATALYSTS; LARGE-SCALE SYNTHESIS; NUCLEOPHILIC GLYCINE; ALDOL REACTIONS; ENANTIOSELECTIVE SYNTHESIS;

D O I：

10.3762/bjoc.10.41

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A family of chiral ligands derived from alpha-phenylethylamine and 2-aminobenzophenone were prepared by alkylation of the nitrogen atom. Upon reaction with glycine and a Ni(II) salt, these ligands were transformed into diastereomeric complexes, as a result of the configurational stability of the stereogenic nitrogen atom. Different diastereomeric ratios were observed depending on the substituent R introduced in the starting ligand, and stereochemical assignments were based on X-ray analysis, along with NMR studies and optical rotation measurements.

引用

页码：442 / 448

页数：7

共 86 条

[1] Synthesis of α-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases [J].

Belokon, YN ;

Bespalova, NB ;

Churkina, TD ;

Císarová, I ;

Ezernitskaya, MG ;

Harutyunyan, SR ;

Hrdina, R ;

Kagan, HB ;

Kocovsky, P ;

Kochetkov, KA ;

Larionov, OV ;

Lyssenko, KA ;

North, M ;

Polásek, M ;

Peregudov, AS ;

Prisyazhnyuk, VV ;

Vyskocil, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12860-12871

[2] ASYMMETRIC-SYNTHESIS OF THREONINE AND PARTIAL RESOLUTION AND RETRORACEMIZATION OF ALPHA-AMINO-ACIDS VIA COPPER(II) COMPLEXES OF THEIR SCHIFF-BASES WITH (S)-2-N-(N'-BENZYLPROLYL)AMINOBENZALDEHYDE AND (S)-2-N-(N'-BENZYLPROLYL)AMINOACETOPHENONE - CRYSTAL AND MOLECULAR-STRUCTURE OF A COPPER(II) COMPLEX OF GLYCINE SCHIFF-BASE WITH (S)-2-N-(N'-BENZYLPROLYL)AMINOACETOPHENONE(S [J].

BELOKON, YN ;

ZELTZER, IE ;

BAKHMUTOV, VI ;

SAPOROVSKAYA, MB ;

RYZHOV, MG ;

YANOVSKY, AI ;

STRUCHKOV, YT ;

BELIKOV, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2010-2017

[3]

Belokon YN, 2001, ANGEW CHEM INT EDIT, V40, P1948, DOI 10.1002/1521-3773(20010518)40:10<1948::AID-ANIE1948>3.0.CO

[4]

2-O

[5] ENANTIOSELECTIVITY OF NICKEL(II) AND COPPER(II) COMPLEXES OF SCHIFF-BASES DERIVED FROM AMINO-ACIDS AND (S)-ORTHO-[(N-BENZYLPROLYL)AMINO]-ACETOPHENONE OR (S)-ORTHO-[(N-BENZYLPROLYL)AMINO]BENZALDEHYDE - CRYSTAL AND MOLECULAR-STRUCTURES OF [NI((S)-BAP-(S)-VAL)] AND [CU((S)-BAP-(S)-VAL)][ [J].

BELOKON, YN ;

MALEYEV, VI ;

VITT, SV ;

RYZHOV, MG ;

KONDRASHOV, YD ;

GOLUBEV, SN ;

VAUCHSKII, YP ;

KAZIKA, AI ;

NOVIKOVA, MI ;

KRASUTSKII, PA ;

YURCHENKO, AG ;

DUBCHAK, IL ;

SHKLOVER, VE ;

STRUCHKOV, YT ;

BAKHMUTOV, VI ;

BELIKOV, VM .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (01) :17-26

[6] GENERAL-METHOD OF DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS BY CONDENSATION OF ALDEHYDES AND KETONES WITH GLYCINE [J].

BELOKON, YN ;

BULYCHEV, AG ;

VITT, SV ;

STRUCHKOV, YT ;

BATSANOV, AS ;

TIMOFEEVA, TV ;

TSYRYAPKIN, VA ;

RYZHOV, MG ;

LYSOVA, LA ;

BAKHMUTOV, VI ;

BELIKOV, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4252-4259

[7] SYNTHESIS OF ENANTIOMERICALLY AND DIASTEREOISOMERICALLY PURE SUBSTITUTED PROLINES VIA CONDENSATION OF GLYCINE WITH OLEFINS ACTIVATED BY A CARBONYL GROUP [J].

BELOKON, YN ;

BULYCHEV, AG ;

PAVLOV, VA ;

FEDOROVA, EB ;

TSYRYAPKIN, VA ;

BAKHMUTOV, VA ;

BELIKOV, VM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (08) :2075-2083

[8] SYNTHESIS OF ENANTIO-ISOMERICALLY AND DIASTEREO-ISOMERICALLY PURE BETA-SUBSTITUTED AND GAMMA-SUBSTITUTED GLUTAMIC ACIDS VIA GLYCINE CONDENSATION WITH ACTIVATED OLEFINS [J].

BELOKON, YN ;

BULYCHEV, AG ;

RYZHOV, MG ;

VITT, SV ;

BATSANOV, AS ;

STRUCHKOV, YT ;

BAKHMUTOV, VI ;

BELIKOV, VM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1865-1872

[9] Improved procedures for the synthesis of (S)-2-[N-(N′-benzylprolyl)amino]benzophenone (BPB) and Ni(II) complexes of Schiff's bases derived from BPB and amino acids [J].

Belokon', YN ;

Tararov, VI ;

Maleev, VI ;

Savel'eva, TF ;

Ryzhov, MG .

TETRAHEDRON-ASYMMETRY, 1998, 9 (23) :4249-4252

[10] Industrial methods for the production of optically active intermediates [J].

Breuer, M ;

Ditrich, K ;

Habicher, T ;

Hauer, B ;

Kesseler, M ;

Stürmer, R ;

Zelinski, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :788-824

← 1 2 3 4 5 6 7 8 9 →