Enantioselective synthesis of 4-unsubstituted 3-alkoxy- and 3-aminoazetidin-2-ones from formaldehyde N,N-dialkylhydrazones

被引：0

作者：

Fernández, R

Ferrete, A

Lassaletta, JM

Llera, JM

Monge, A

机构：

[1] Univ Sevilla, CSIC, Inst Invest Quim, Seville 41092, Spain

[2] Univ Sevilla, Dept Quim Organ & Farmaceut, Seville 41081, Spain

[3] Univ Sevilla, Dept Quim Organ, Seville, Spain

[4] CSIC, Inst Ciencia Mat Madrid, Madrid, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2000年 / 39卷 / 16期

关键词：

asymmetric synthesis; cycloadditions; hydrazones; ketenes; lactams;

D O I：

10.1002/1521-3773(20000818)39:16<2893::AID-ANIE2893>3.0.CO;2-E

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Playing two roles at once, chiral amines from L-proline or D-mannitol act as protecting groups and as chiral auxiliaries in the [2+2] cyclo-addition of formaldehyde hydrazones, such as 1, to ketenes. This strategy, based on the stability of the hydrazones as methanimines and on the development of a new oxidative cleavage of hydrazides, provides a short entry to enantiopure 4-unsubstituted 3-alkoxy- and 3-aminoazetidinones with desired configurations. X=OBn, N(CO<SUB2>Bn)Bn; Bn=benzyl; MMPP=magnesium monoperoxyphthalate.

引用

页码：2893 / 2897

页数：5

共 50 条

[41] Polymer-Supported Stereoselective Synthesis of Tetrahydro-2H-oxazolo[3,2-a]pyrazin-5(3H)-ones from N-(2-Oxo-ethyl)-Derivatized Dipeptides via Eastbound Iminiums
La Venia, Agustina
Dolensky, Bohumil
Krchnak, Viktor
ACS COMBINATORIAL SCIENCE, 2013, 15 (03) : 162 - 167
[42] Synthesis of 6H-thieno[3,2-b]pyridin-7-ones from N-(2-X-carbonyl)-3-thienyl ketenimines (X = RS, ArO, R2N) via consecutive [1,5]-X sigmatropic rearrangement and 6π-electrocyclization
Alajarin, Mateo
Vidal, Angel
Ortin, Maria-Mar
SYNTHESIS-STUTTGART, 2007, (04): : 590 - 596
[43] Synthesis and Characterization of Some New N-(Substituted 4-Methylene-2-oxo-4H-benzo[e][1,3]oxazin-3-yl)isonicotinamide
Al-Bogami, Abdullah S.
ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (07) : 3045 - 3049
[44] Synthesis and tautomeric structure of 2-[N-aryl-2-oxo-2-arylethanehydrazonoyl]-6-methyl-4(3H)-pyrimidinones
Shawali, AS
Farghaly, TA
TETRAHEDRON, 2004, 60 (13) : 3051 - 3057
[45] Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one
Reyes-Rangel, Gloria
Maranon, Virginia
Avila-Ortiz, C. Gabriela
de Parrodi, Cecilia Anaya
Quintero, Leticia
Juaristi, Eusebio
TETRAHEDRON, 2006, 62 (35) : 8404 - 8409
[46] Operationally convenient asymmetric synthesis of (S)- and (R)-3-amino-4,4,4-trifluorobutanoic acid -: Part II.: Enantioselective biomimetic transamination of 4,4,4-trifluoro-3-oxo-N-[(R)-1-phenylethyl]butanamide
Soloshonok, Vadim A.
Ohkura, Hironari
Yasumoto, Manabu
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (07) : 930 - 935
[47] Synthesis of N4-amino and N4-hydroxy derivatives of 5-azacytidine.: A facile rearrangement of the N4-amino derivative to 5-(3-β-D-ribofuranosylureido)-1H-1,2,4-triazole
Pískala, A
Hanna, NB
Masojídkova, M
Fiedler, P
Votruba, I
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2004, 69 (04) : 905 - 917
[48] Multibridged [3n]cyclophanes, 7 Improved synthesis, structure, and cycloaddition reaction of [34](1,2,4,5)cyclophane
Sentou, W
Satou, T
Yasutake, M
Lim, C
Sakamoto, Y
Itoh, T
Shinmyozu, T
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (05) : 1223 - 1231
[49] Enantioselective total synthesis of (2S,3R,4R)-D-xylo-phytosphingosine from substituted azetidin-2-one
Pandey, Ganesh
Tiwari, Dharmendra Kumar
TETRAHEDRON LETTERS, 2009, 50 (26) : 3296 - 3298
[50] Direct synthesis of C3-mono-functionalized oxindoles from N-unprotected 2-oxindole and their antileishmanial activity
Scala, Angela
Cordaro, Massimiliano
Grassi, Giovanni
Piperno, Anna
Barberi, Giuseppina
Cascio, Antonio
Risitano, Francesco
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (03) : 1063 - 1069

← 1 2 3 4 5 →