A practical synthesis of Cbz protected (1R,2R) and (1S,2S) 2-hydroxy-cyclobutylamines DOI
Can Jin, Yilin Wang,

Xiangsheng Xu

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: unknown, P. 155391 - 155391

Published: Nov. 1, 2024

Language: Английский

Three-dimensional saturated C(sp3)-rich bioisosteres for benzene DOI
Jet Tsien, Chao Hu, Rohan R. Merchant

et al.

Nature Reviews Chemistry, Journal Year: 2024, Volume and Issue: 8(8), P. 605 - 627

Published: July 9, 2024

Language: Английский

Citations

38
Light‐Driven Synthesis and Functionalization of Bicycloalkanes, Cubanes and Related Bioisosteres DOI Creative Commons
Sara Cuadros, Julien Paut, Elsa Anselmi

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)

Published: Jan. 5, 2024

Bicycloalkanes, cubanes and their structural analogues have emerged as bioisosteres of (hetero)arenes. To meet increasing demand, the chemical community has developed a plethora novel synthetic methods. In this review, we assess progress made in field light-driven construction functionalization such relevant molecules. We focused on diverse targets, well reaction processes giving access to: (i) [1.1.1]-bicyclopentanes (BCPs); (ii) [2.2.1]-bicyclohexanes (BCHs); (iii) [3.1.1]-bicycloheptanes (BCHeps); (iv) cubanes; other structurally related scaffolds. Finally, future perspectives dealing with identification manifolds to new functionalized bioisosteric units are discussed.

Language: Английский

Citations

27
Enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones enabled by asymmetric Lewis acid catalysis DOI Creative Commons
Wen‐Biao Wu, Bing Xu, Xue-Chun Yang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Sept. 12, 2024

Language: Английский

Citations

21
Enantioselective synthesis of 2-substituted bicyclo[1.1.1]pentanes via sequential asymmetric imine addition of bicyclo[1.1.0]butanes and skeletal editing DOI

Jinteng Che,

Wei‐Yi Ding, Hongbo Zhang

et al.

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Language: Английский

Citations

2
Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings DOI
Shota Nagasawa, Yoshiharu Iwabuchi

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: July 4, 2024

Abstract Recently, many saturated bioisosteres of the benzene ring have been developed, and their applications in drug development evaluated. Most these are caged hydrocarbons, which rigid skeletons three-dimensional spaces. Recent efforts to synthesize hydrocarbons enabled access multi-functionalized congeners that expected be (bio)isosteres benzenes. This short review summarizes recently reported methods for obtaining (typically more than disubstituted) hydrocarbons. 1 Introduction 2 Proposed Structures Caged Hydrocarbons as Saturated (Bio)isosteres Benzene Ring: A Brief Summary 3 Access Multi-functionalized Hydrocarbons: De Novo Synthetic Approaches 3.1 Bicyclo[1.1.1]pentanes (BCPs) 3.2 Bicyclo[2.1.1]hexanes (BCHs) 3.3 Bicyclo[3.1.1]heptanes (BCHeps) 3.4 Others 4 C–H Functionalization 5 Conclusion

Language: Английский

Citations

7
Recent Advances in Enantioselective Radical Reactions of C(sp3)—H Bond DOI
Ling Tang,

Haitao Qin,

Feng Liu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 498 - 498

Published: Jan. 1, 2025

Language: Английский

Citations

0
Chiral Lewis Acid-Catalyzed Intramolecular [2 + 2] Photocycloaddition: Enantioselective Synthesis of Azaarene-Functionalized Azabicyclo[2.1.1]hexanes and Bicyclo[1.1.1]pentanes DOI
Dong Tian, Yue Pan, Xiaowei Zhao

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

We present an asymmetric intramolecular [2 + 2] photocycloaddition reaction enabled by a dual catalyst system involving DPZ as photosensitizer and chiral Sc(III) complex, leading to azaarene-functionalized 2-azabicyclo[2.2.1]hexanes (aza-BCHs). The approach efficiently preventing racemization during subsequent nitrogen-deletion skeletal editing of aza-BCHs yield 2-substituted bicyclo[1.1.1]pentanes (BCPs). method achieves high ee broad substrate scope, including the successful formation all-carbon quaternary stereocenters. Furthermore, activation simple azaarene substrates Lewis acids in photocatalysis highlights notable contribution this field.

Language: Английский

Citations

0
Light‐Driven Synthesis and Functionalization of Bicycloalkanes, Cubanes and Related Bioisosteres DOI Creative Commons
Sara Cuadros, Julien Paut, Elsa Anselmi

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(14)

Published: Jan. 5, 2024

Abstract Bicycloalkanes, cubanes and their structural analogues have emerged as bioisosteres of (hetero)arenes. To meet increasing demand, the chemical community has developed a plethora novel synthetic methods. In this review, we assess progress made in field light‐driven construction functionalization such relevant molecules. We focused on diverse targets, well reaction processes giving access to: (i) [1.1.1]‐bicyclopentanes (BCPs); (ii) [2.2.1]‐bicyclohexanes (BCHs); (iii) [3.1.1]‐bicycloheptanes (BCHeps); (iv) cubanes; other structurally related scaffolds. Finally, future perspectives dealing with identification manifolds to new functionalized bioisosteric units are discussed.

Language: Английский

Citations

2
Routes to Advanced Intermediates in the Synthesis of Tetracarbocyclic Sesquiterpenoids Daphnenoid A and Artatrovirenols A and B DOI Creative Commons
Jiarui Zong, Kirsten E. Christensen, Jeremy Robertson

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(8), P. 1556 - 1560

Published: Feb. 19, 2024

A short route from dihydrocarvone is described, which led to the tetracarbocyclic core common artatrovirenol and B daphnenoid A. variant of this afforded guaia-4,6-dien-3-one (from Enterospermum madagascarensis) its epimer. From 2-(2-oxoethyl)furan, a 15-step sequence then delivered complete carbon skeleton all functionality necessary for Key steps in include diastereoselective intramolecular oxidopyrylium cycloaddition, oxa-bridge cleavage under "push–pull" conditions, Diels–Alder cycloaddition.

Language: Английский

Citations

2
tert‐Butyl as a Functional Group: Non‐Directed Catalytic Hydroxylation of Sterically Congested Primary C−H Bonds DOI Creative Commons
Siu‐Chung Chan, Andrea Palone, Massimo Bietti

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(28)

Published: May 1, 2024

Abstract The tert ‐butyl group is a common aliphatic motif extensively employed to implement steric congestion and conformational rigidity in organic organometallic molecules. Because of the combination high bond dissociation energy (~100 kcal mol −1 ) limited accessibility, absence directing groups, neither radical nor approaches are effective for chemical modification C−H bonds. Herein we overcome these limits by employing highly electrophilic manganese catalyst, [Mn( CF3 bpeb)(OTf) 2 ], that operates strong hydrogen donor solvent nonafluoro‐ alcohol (NFTBA) catalytically activates peroxide generate powerful manganese‐oxo species effectively oxidizes Leveraging on interplay steric, electronic, medium torsional effects, site‐selective product chemoselective hydroxylation accomplished with broad reaction scope, delivering primary alcohols as largely dominant products preparative yields. Late‐stage at sites demonstrated 6 densely functionalized molecules pharmaceutical interest. This work uncovers novel disconnection approach, harnessing potential functional strategic synthetic planning complex molecular architectures.

Language: Английский

Citations

2