Asymmetric hydrogenolysis of racemic 3-substitued-3-hydroxy-isoindolin-1-ones employing SPINOL-derived chiral phosphoric acid

被引：12

作者：

Zhang, Yiliang ^{[1
,2
]}

He, Li ^{[1
,2
]}

Shi, Lei ^{[1
,2
]}

机构：

[1] Harbin Inst Technol, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

[2] Harbin Inst Technol, Sch Chem & Chem Engn, MIIT Key Lab Crit Mat Technol New Energy Convers, Harbin 150001, Heilongjiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 16期

关键词：

Asymmetric catalysis; Chiral phosphoric acid; Hydrogenolysis; Hantzsch ester; IONIC HYDROGENATION; BENZYLIC ALCOHOLS; TERTIARY ALCOHOLS; SYNTHETIC METHODS; FORMIC-ACID; ISOINDOLINONES; EFFICIENT; FLUORIDE; TRIETHYLSILANE; PHSCF2SIME3;

D O I：

10.1016/j.tetlet.2018.03.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric hydrogenolysis of racemic 3-substitued-3-hydroxyisoindolin-1-ones has been developed employing SPINOL-derived phosphoric acid and a high steric demand Hantzsch ester as the hydrogen source. The corresponding products are obtained in good yields and up to 93% enantioselectivities. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1592 / 1595

页数：4

共 32 条

[31] ASYMMETRIC-SYNTHESIS OF (1R,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES AND (1S,8S)-1-HYDROXYPYRROLIZIDIN-3-ONES VIA THE ALDOL REACTION BETWEEN N-BOC-(S)-PROLINAL AND CHIRAL ACETATE ENOLATE EQUIVALENTS DERIVED FROM (S)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3] AND (R)-[(ETA-5-C5H5)FE(CO)(PPH3)COCH3]
BECKETT, RP
DAVIES, SG
MORTLOCK, AA
TETRAHEDRON-ASYMMETRY, 1992, 3 (01) : 123 - 136
[32] Access to 2'′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones via amino acid derived phosphine-catalyzed asymmetric [4+2] annulation with easily available oxindole-derived α,β-unsaturated imines
Zhang, Xiao-Nan
Dong, Xiang
Wei, Yin
Shi, Min
TETRAHEDRON, 2014, 70 (17) : 2838 - 2846

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