TetraPh-Tol-BITIOPO: a new atropisomeric 3,3′-bithiophene based phosphine oxide as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions

Mirco, Abbinante Vincenzo; Benaglia, Maurizio; Rossi, Sergio; Benincori, Tiziana; Cirilli, Roberto; Pierini, Marco

doi:10.1039/c9ob01297d

Cited by 4 publications

(1 citation statement)

References 59 publications

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“…In addition, the ORD of any chiral compounds, such as the reaction atropisomer 45 from 42, could be also used in the AC assignment (Figure 8A) (Mirco et al, 2019). The enantiomers (+)-45 and (-)-45 exhibited a very good mirror image as expected.…”

Section: Specific Optical Rotation ([α] Dmentioning

confidence: 77%

Computational methods and points for attention in absolute configuration determination

Zhu

Nafie

2023

Front. Nat. Prod.

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With the rapid development of high performance computers and computational methods, including software, an increasing number of experimental chemists have tried to use computational methods such as optical rotation (OR, including the matrix model), optical rotatory dispersion (ORD), electronic circular dichroism (ECD or CD), vibrational circular dichroism (VCD), and magnetic shielding constants—nuclear magnetic resonance (NMR)—to explain and/or assign absolute configuration (AC) for various compounds. Such reports in the field of natural products have increased dramatically. However, every method has its range of application. This leads, in some cases, to incorrect conclusions by researchers who are not familiar with these methods. In this review, we provide experimental chemists and researchers with more computational details and suitable suggestions, and especially hope that this experience may help readers avoid computational pitfalls. Finally, we discuss the use of simplified models to replace original complex structures with a long side chain. The fundamental basis for using models to represent complex chiral compounds, such as in OR calculations, is the existence of conformation pairs with near canceling conformer contributions that justify the use of models rather than the original compounds. Using examples, we here introduce the transition state (TS) calculation, which may benefit readers in this area for use and mastery for their AC study. This review will summarize the general concepts involved in the study of AC determinations.

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Section: Specific Optical Rotation ([α] Dmentioning

confidence: 77%

Computational methods and points for attention in absolute configuration determination

Zhu

Nafie

2023

Front. Nat. Prod.

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Five-membered ring systems: thiophenes and selenium/tellurium analogs and benzo analogs

Joule

2021

Progress in Heterocyclic Chemistry

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DFT investigation on Lewis base-catalyzed Lewis acid-mediated reactions: hypervalent silicon species as chiral organocatalysts in (direct) aldol reactions

2020

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TetraPh-Tol-BITIOPO: a new atropisomeric 3,3′-bithiophene based phosphine oxide as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions

Abstract: A new chiral phosphine oxide based on a 3,3′-bithiophene scaffold (TetraPh-Tol-BITIOPO) was synthesized, fully characterized and separated into antipodes through chiral HPLC.

Cited by 4 publications

References 59 publications

Computational methods and points for attention in absolute configuration determination

Computational methods and points for attention in absolute configuration determination

Five-membered ring systems: thiophenes and selenium/tellurium analogs and benzo analogs

DFT investigation on Lewis base-catalyzed Lewis acid-mediated reactions: hypervalent silicon species as chiral organocatalysts in (direct) aldol reactions

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