Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Phosphoramidite Ligands
2.2. Synthesis of Chiral Brønsted Acids
2.3. Applications
3. Experimental Section
3.1. General Procedure for the Synthesis of C2 Symmetric and Pseudo C2 Symmetric Secondary Amines (Procedure A) [35]
3.2. (R)-Bis((R)-1-Phenylethyl) Amine
3.3. (R)-1-(Naphthalen-2-yl)-N-((R)-1-Phenylethyl) Ethanamine
3.4. General Procedure for the Preparation of Phosphoramidites (Procedure B)
3.5. (4aR,7aR,11aS,11bS)-N,N-Diethyl-2,10-Diphenylhexahydrobis([1,3]Dioxino)[5,4-d:4′,5′- f][1,3,2]Dioxaphosphepin-6-amine (L1)
3.6. (4aR,7aR,11aS,11bS)-N,N-Diethyl-2,10-di-p-Tolylhexahydrobis([1,3]Dioxino)[5,4-d:4′,5′- f][1,3,2]Dioxaphosphepin-6-amine (L2)
3.7. 1-((4aR,7aR,11aS,11bS)-2,10-Diphenylhexahydrobis([1,3]dioxino)[5,4-d:4′,5′- f][1,3,2]dioxaphosphepin-6-yl)piperidine (L3)
3.8. 1-((4aR,7aR,11aS,11bS)-2,10-Di-p-Tolylhexahydrobis([1,3]dioxino)[5,4-d:4′,5′- f][1,3,2]dioxaphosphepin-6-yl)piperidine (L4)
3.9. (4aR,7aR,11aS,11bS)-2,10-Diphenyl-N,N-bis((S)-1-phenylethyl)hexahydrobis([1,3]dioxino) [5,4-d:4′,5′-f][1,3,2]dioxaphosphepin-6-amine (L5)
3.10. (4aR,7aR,11aS,11bS)-N,N-Bis((S)-1-Phenylethyl)-2,10-di-ptolylhexahydrobis([ 1,3]dioxino)[5,4-d:4′,5′-f][1,3,2]dioxaphosphepin-6-amine (L6)
3.11. (4aR,7aR,11aS,11bS)-N-((S)-1-(Naphthalen-2-yl)ethyl)-2,10-diphenyl-N-((S)-1- Phenylethyl)hexahydrobis([1,3]dioxino)[5,4-d:4′,5′-f][1,3,2]dioxaphosphepin-6-amine (L7)
3.12. (4aR,7aR,11aS,11bS)-N-((S)-1-(Naphthalen-2-yl)ethyl)-N-((S)-1-phenylethyl)-2,10-di-ptolylhexahydrobis([ 1,3]dioxino)[5,4-d:4′,5′-f][1,3,2]dioxaphosphepin-6-amine (L8)
3.13. General Procedure for the Preparation of Chiral Brønsted Acid (Procedure C) [20]
3.14. (4aR,7aR,11aS,11bS)-6-Hydroxy-2,10-diphenylhexahydrobis([1,3]dioxino)[5,4-d:4′,5′- f][1,3,2]Dioxaphosphepine 6-Oxide (1a)
3.15. (4aR,7aR,11aS,11bS)-6-Hydroxy-2,10-di-p-tolylhexahydrobis([1,3]dioxino)[5,4-d:4′,5′- f][1,3,2]Dioxaphosphepine 6-Oxide (1b)
4. Conclusions
Acknowledgments
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Al-Majid, A.M.A.; Barakat, A.; Mabkhot, Y.N.; Islam, M.S. Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol. Int. J. Mol. Sci. 2012, 13, 2727-2743. https://doi.org/10.3390/ijms13032727
Al-Majid AMA, Barakat A, Mabkhot YN, Islam MS. Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol. International Journal of Molecular Sciences. 2012; 13(3):2727-2743. https://doi.org/10.3390/ijms13032727
Chicago/Turabian StyleAl-Majid, Abdullah Mohammed A., Assem Barakat, Yahia Nasser Mabkhot, and Mohammad Shahidul Islam. 2012. "Synthesis and Characterization of Privileged Monodentate Phosphoramidite Ligands and Chiral Brønsted Acids Derived from D-Mannitol" International Journal of Molecular Sciences 13, no. 3: 2727-2743. https://doi.org/10.3390/ijms13032727