(4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative:: practical asymmetric synthesis of α-amino acids

被引：27

作者：

Guillena, G ^{[1
]}

Nájera, C ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(98)00113-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The lithium enolate of enantiomerically pure N-[bis(methylthio)methylene] glycinate 11 derived from (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one reacts with alkyl halides giving the alkylated derivatives 12 with a high degree of control of the diastereoselectivity. These alkylated systems are easily hydrolyzed to the corresponding cx-amino acids, the chiral auxiliary being recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1125 / 1129

页数：5

共 50 条

[21] The (2S,2'S,4R,5S,5'R)-2,2'-Di-tert-butyl-4-hydroxy-5,5'-dimethyl-4,5'-bi(1,3-dioxolanyl)-4'-one
Aitken, R. Alan
Power, Lynn A.
Slawin, Alexandra M. Z.
MOLBANK, 2023, 2023 (03)
[22] SYNTHESIS OF (1S 2R 4R 5S 6R)-1,2,4,5,6-PENTA-O-BENZOYLMYOINOSITOL
MERCIER, D
GERO, SD
TETRAHEDRON LETTERS, 1968, (31) : 3459 - &
[23] Versatile chiral synthons for 1,2-diamines:: (4S,5S)- and (4R,5R)-4,5-dimethoxy-2-imidazolidinones
Seo, R
Ishizuka, T
Abdel-Aziz, AAM
Kunieda, T
TETRAHEDRON LETTERS, 2001, 42 (36) : 6353 - 6355
[24] Asymmetric induction in Darzens condensation by means of (R)-5,5-dimethyl-4-phenyloxazolidin-2-one as an effective chiral auxiliary
Badrian, Abed
Mamaghani, Manouchehr
Tabatabaeian, Khalil
Valizadeh, Hassan
LETTERS IN ORGANIC CHEMISTRY, 2007, 4 (04) : 228 - 231
[25] (2S,3S)-1-PHENYLTHIO-2,3-BUTANEDIOL - A USEFUL CHIRAL BUILDING BLOCK FOR A SIMPLE SYNTHESES OF (4R,5S)-5-HYDROXYHEXAN-4-OLIDE AND (4R,5S)-5-HYDROXY-2-HEXEN-4-OLIDE
FUJISAWA, T
KOJIMA, E
SATO, T
CHEMISTRY LETTERS, 1987, (11) : 2227 - 2228
[26] REGIOSELECTIVE AND DIASTEREOSELECTIVE ALKYLATION OF (1R,5S)-4-ETHYL-6,6-DIMETHYL-3-(PHENYLSULFONYL)BICYCLO[3.1.1]HEPT-3-EN-2-ONE
KATO, M
WATANABE, M
AWEN, BZ
VOGLER, B
TETRAHEDRON LETTERS, 1991, 32 (50) : 7439 - 7442
[27] Asymmetric synthesis of amino sugars.: Part 1:: Stereoselective synthesis of (2S,3S,4R,5S)-2-amino-1,3,4,5,6-hexanepentol derivatives and their conversion to L-mannosamine derivatives
Ermolenko, L
Sasaki, NA
Potier, P
TETRAHEDRON LETTERS, 1999, 40 (28) : 5187 - 5190
[28] (4S,5R,2′R)3,4-dimethyl-1-[2′-(1-naphthyl)-2′-phenylacetyl]-5-phenylimidazolidin-2-one
Baggio, R
Lotz, G
Palacios, S
Mariezcurrena, RA
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1998, 54 : 1677 - 1679
[29] Expedient Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid via Alkylation of Chiral Nucleophilic Glycine Equivalent
Mei, Haibo
Hiramatsu, Takahiro
Takeda, Ryosuke
Moriwaki, Hiroki
Abe, Hidenori
Han, Jianlin
Soloshonok, Vadim A.
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (04) : 629 - 634
[30] A NEW PRACTICAL SYNTHESIS OF (2S,3R,4R,5S)-3,4-DIHYDROXY-2,5-BIS(HYDROXYMETHYL)PYRROLIDINE
ZOU, W
SZAREK, WA
CARBOHYDRATE RESEARCH, 1993, 242 : 311 - 314

← 1 2 3 4 5 →