Regioselective Ring-Opening of Oxetanes Catalyzed by Lewis Superacid Al(C6F5)3

被引：0

作者：

Bellido, Marina ^{[1
,2
]}

Riego-Mejias, Carlos ^{[1
,2
]}

Sciortino, Giuseppe ^{[3
]}

Verdaguer, Xavier ^{[1
,2
]}

Lledos, Agusti ^{[3
]}

Riera, Antoni ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol BIST, Inst Res Biomed IRB Barcelona, Baldiri Reixac 10, Barcelona 08028, Spain

[2] Univ Barcelona, Dept Quim Inorgan & Organ, Seccio Quim Organ, Marti i Franques 1, Barcelona 08028, Spain

[3] Univ Autonoma Barcelona, Dept Quim, Barcelona 08193, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 04期

关键词：

Lewis superacid; tris(pentafluorophenyl)alane; oxetanes; isomerization; catalysis; asymmetric hydrogenation; natural product synthesis; ENANTIOSELECTIVE SYNTHESIS; COMPLEXES; DERIVATIVES; CHEMISTRY; ALDEHYDES; ACIDITY; RC-33;

D O I：

10.1002/adsc.202301183

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

This study details an aluminum-catalyzed regioselective isomerization of 2,2-disubstituted oxetanes to yield homoallylic alcohols. The reaction takes place in toluene at 40( degrees)C, employing 1 mol % of Al(C6F5)(3) as catalyst. This catalytic system shows a wide substrate scope (12 examples). The optimized conditions are especially useful for electron-rich aryl oxetanes, completely suppressing the formation of allyl isomers and reducing the amount of the dimer by-product. The synthetic applicability of the reported methodology is demonstrated by the enantioselective formal synthesis of curcuquinone and the sigma 1 receptor agonist RC-33.

引用

页码：925 / 933

页数：9

共 60 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2] Application of the lithiation-borylation reaction to the rapid and enantioselective synthesis of the bisabolane family of sesquiterpenes [J].

Aggarwal, Varinder K. ;

Ball, Liam T. ;

Carobene, Simon ;

Connelly, Rickki L. ;

Hesse, Matthew J. ;

Partridge, Benjamin M. ;

Roth, Philippe ;

Thomas, Stephen P. ;

Webster, Matthew P. .

CHEMICAL COMMUNICATIONS, 2012, 48 (74) :9230-9232

[3] Ring-opening reactions of oxetanes: A review of methodology development and synthetic applications [J].

Ahmad, Sajjad ;

Yousaf, Muhammad ;

Mansha, Asim ;

Rasool, Nasir ;

Zahoor, Ameer Fawad ;

Hafeez, Freeha ;

Rizvi, Sayyad Muhammad Ali .

SYNTHETIC COMMUNICATIONS, 2016, 46 (17) :1397-1416

[4]

Aldridge S., 2011, GROUP 13 METALS ALUM

[5]

Baek J. W, 2022, ORGANOMETALLICS, V41, P2455

[6] Put a ring on it: application of small aliphatic rings in medicinal chemistry [J].

Bauer, Matthias R. ;

Di Fruscia, Paolo ;

Lucas, Simon C. C. ;

Michaelides, Iacovos N. ;

Nelson, Jennifer E. ;

Storer, R. Ian ;

Whitehurst, Benjamin C. .

RSC MEDICINAL CHEMISTRY, 2021, 12 (04) :448-471

[7] TRIS(PENTAFLUOROPHENYL)ALANE - A NOVEL ALUMINUM ORGANYL [J].

BELGARDT, T ;

STORRE, J ;

ROESKY, HW ;

NOLTEMEYER, M ;

SCHMIDT, HG .

INORGANIC CHEMISTRY, 1995, 34 (14) :3821-3822

[8] Enantioselective Ir-Catalyzed Hydrogenation of Terminal Homoallyl Sulfones: Total Synthesis of (-)-Curcumene [J].

Bellido, Marina ;

Riego-Mejias, Carlos ;

Diaz-Moreno, Alejandro ;

Verdaguer, Xavier ;

Riera, Antoni .

ORGANIC LETTERS, 2023, 25 (09) :1453-1457

[9]

Bhaduri S., 2014, Homogeneous catalysis: Mechanisms and industrial applications

[10] From unsuccessful H2-activation with FLPs containing B(Ohfip)3 to a systematic evaluation of the Lewis acidity of 33 Lewis acids based on fluoride, chloride, hydride and methyl ion affinities [J].

Boehrer, Hannes ;

Trapp, Nils ;

Himmel, Daniel ;

Schleep, Mario ;

Krossing, Ingo .

DALTON TRANSACTIONS, 2015, 44 (16) :7489-7499

← 1 2 3 4 5 6 →