Regioselective Ring-Opening of Amino Acid-Derived Chiral Aziridines: an Easy Access to cis-2,5-Disubstituted Chiral Piperazines

被引：27

作者：

Samanta, Krishnananda ^{[1
]}

Panda, Gautam ^{[1
]}

机构：

[1] Cent Drug Res Inst, Div Med & Proc Chem, Lucknow 226001, Uttar Pradesh, India

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 01期

关键词：

amino acids; cyclization; heterocycles; natural products; regioselectivity; MITSUNOBU; POTENT; INHIBITORS; CHEMISTRY;

D O I：

10.1002/asia.201000554

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3 center dot OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by alpha-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin.

引用

页码：189 / 197

页数：9

共 36 条

[1] Synthesis and application of chiral cis-2,5-disubstituted pyrrolidine organocatalysts
Singh, Suraj
Kumar, Rohtash
Dubey, Navneet Nandgopal
Appayee, Chandrakumar
CHEMICAL COMMUNICATIONS, 2024, 60 (66) : 8768 - 8771
[2] An efficient synthetic approach for N-C bond formation from (S)-amino acids: an easy access to cis-2,5disubstituted chiral piperazines
Manna, Sudipta Kumar
Panda, Gautam
RSC ADVANCES, 2013, 3 (40): : 18332 - 18338
[3] Enantiopure Cis-2,5-Disubstituted 2,5-Dihydropyrroles from D-Glycal-Derived Vinyl Aziridines
Di Bussolo, Valeria
Frau, Ileana
Crotti, Stefano
Uccello-Barretta, Gloria
Balzano, Federica
Pineschi, Mauro
Crotti, Paolo
ORGANIC LETTERS, 2013, 15 (23) : 6026 - 6029
[4] REGIO- AND STEREOSELECTIVE RING-OPENING REACTION OF CHIRAL AZIRIDINES: A FACILE SYNTHESIS OF CHIRAL β-AMINO ALCOHOLS
Higashiyama, Kimio
Matsumura, Masataka
Kojima, Hiroshi
Yamauchi, Takayasu
HETEROCYCLES, 2009, 78 (02) : 471 - 485
[5] Syntheses of Chiral β- and γ-Amino Ethers, Morpholines, and Their Homologues via Nucleophilic Ring-Opening of Chiral Activated Aziridines and Azetidines
Ghorai, Manas K.
Shukla, Dipti
Bhattacharyya, Aditya
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (08): : 3740 - 3753
[6] One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes
Wang, Ping-An
Zhang, Sheng-Yong
Kagan, Henri B.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 265 - 269
[7] Gold-catalysed synthesis of amino acid-derived 2,5-disubstituted oxazoles
Paradise, Christopher L.
Sarkar, Pooja R.
Razzak, Mina
De Brabander, Jef K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (11) : 4017 - 4020
[8] Highly regioselective ring-opening of aziridines with arenesulfinates on water: a facile access to β-amino/vinyl sulfones
Chawla, Ruchi
Singh, Atul K.
Yadav, Lal Dhar S.
TETRAHEDRON, 2013, 69 (06) : 1720 - 1724
[9] Tartaric acid-derived chiral carbon nanodots for catalytic enantioselective ring-opening reactions of styrene oxide
Zhao, Xinyi
Reva, Yana
Jana, Bikash
Langford, Daniel
Kinzelmann, Marina
Zhang, Zhipeng
Liu, Qi
Drewello, Thomas
Guldi, Dirk M.
Chen, Xiaoqing
CHEMICAL COMMUNICATIONS, 2024, 60 (75) : 10382 - 10385
[10] Catalytic asymmetric ring-opening of aminocyclopropanes with oxygen nucleophiles: access to chiral γ-amino acid derivatives
Luo, Ru-Lin
Wang, Xiao-Bing
Xie, Ming-Sheng
Guo, Hai-Ming
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (06): : 1817 - 1823

← 1 2 3 4 →