Keywords
aza-Michael addition
intramolecular cyclization
phosphines
Pyrphos
reduction
X-ray analysis.
Abstract
A new efficient synthesis of racemic (R*,R*)-Pyrphos ligand based on aza-Michael addition reaction of 2,3-bis(diphenylphosphoryl)buta-1,3-diene with ammonia followed by the reduction of resulting 3,4-bis(diphenylphosphoryl)pyrrolidine is proposed. The starting reactants are available but-2-yne-1,4-diol and chloro(diphenyl)phosphine.
References
.
Sheldrick G.M.
Acta Crystallographica Section A: Foundations and Advances,
2015
.
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography,
2009
.
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography,
2007
.
Belser T., Stöhr M., Pfaltz A.
Journal of the American Chemical Society,
2005
.
Clevenger A.L., Stolley R.M., Aderibigbe J., Louie J.
Chemical Reviews,
2020
.
Strukul G., Varagnolo A., Pinna F.
Journal of Molecular Catalysis A Chemical,
1997
.
Nagel U., Kinzel E., Andrade J., Prescher G.
Chemische Berichte,
1986
.
Yi B., Fan Q., Deng G., Li Y., Qiu L., Chan A.S.
Organic Letters,
2004
.
Daubignard J., Detz R.J., de Bruin B., Reek J.N.
Organometallics,
2019
.
Leeuwen P.W., Cano I., Freixa Z.
ChemCatChem,
2020
.
Ribourdouille Y., Engel G.D., Richard-Plouet M., Gade L.H.
Chemical Communications,
2003
.
Haddow M.F., Middleton A.J., Orpen A.G., Pringle P.G., Papp R.
Dalton Transactions,
2009
.
Hérault D., Nguyen D.H., Nuel D., Buono G.
Chemical Society Reviews,
2015
.
Gallen A., Riera A., Verdaguer X., Grabulosa A.
Catalysis Science and Technology,
2019
.
Shet H., Parmar U., Bhilare S., Kapdi A.R.
Organic Chemistry Frontiers,
2021
.
Zanardo A., Michelin R.A., Pinna F., Strukul G.
Inorganic Chemistry,
1989
.
.
Nagel U., Krink T.
Chemische Berichte,
1995
.
Nagel U., Kinzel E.
Chemische Berichte,
1986
.
.
Fan Q., Deng G., Lin C., Chan A.S.
Tetrahedron Asymmetry,
2001
.
.
Xing L., Xie J., Chen Y., Wang L., Zhou Q.
Advanced Synthesis and Catalysis,
2008
.
Kassube J., Gade L.
Advanced Synthesis and Catalysis,
2009
.
Engel G., Gade L.H.
Chemistry - A European Journal,
2002
.
.
.
Jantke D., Marziale A.N., Reiner T., Kraus F., Herdtweck E., Raba A., Eppinger J.
Journal of Organometallic Chemistry,
2013
.
Yi B., He H., Fan Q.
Journal of Molecular Catalysis A Chemical,
2010
.
Pollok T., Schmidbaur H.
Tetrahedron Letters,
1987
.
Rocha Gonsalves A.M., Bayón J.C., Pereira M.M., Serra M.E., Pereira J.P.
Journal of Organometallic Chemistry,
1998
.
Gonsalves A.M., Serra M.E., Silva M.R., Beja A.M., Paixão J.A., Veiga L.A.
Journal of Molecular Catalysis A Chemical,
2001
.
INOGUCHI K., ACHIWA K.
Chemical and Pharmaceutical Bulletin,
2011
.
Yi B., Wu G., Zhou W., He H.
Chinese Journal of Organic Chemistry,
2013
.
Sukhikh T.S., Davydova M.P., Artem'ev A.V.
Mendeleev Communications,
2023
.
Matveeva A.G., Bykhovskaya O.V., Pasechnik M.P., Vologzhanina A.V., Aysin R.R., Matveev S.V., Godovikov I.A., Yu. Kudryavtsev I., Baulina T.V., Brel V.K.
Mendeleev Communications,
2022
.
Bandaru S.S., Shah J., Bhilare S., Schulzke C., Kapdi A.R., Roger J., Hierso J.
Coordination Chemistry Reviews,
2023