Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes

Nuria Brugat; Josep Duran; Alfonso Polo; Julio Real; Ángel Álvarez-Larena; J. Francesc Piniella

doi:10.1016/S0957-4166(02)00143-X

Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes

Nuria Brugat, Josep Duran, Alfonso Polo, Julio Real, Ángel Álvarez-Larena, J. Francesc Piniella

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Abstract

The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92% e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)4] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)2] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by 31P NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)2] gave the enantiomeric complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. © 2002 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	569-577
Journal	Tetrahedron Asymmetry
Volume	13
Issue number	6
DOIs	https://doi.org/10.1016/S0957-4166(02)00143-X
Publication status	Published - 19 Apr 2002

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title = "Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes",

abstract = "The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92% e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)4] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)2] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by 31P NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)2] gave the enantiomeric complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. {\textcopyright} 2002 Elsevier Science Ltd. All rights reserved.",

author = "Nuria Brugat and Josep Duran and Alfonso Polo and Julio Real and {\'A}ngel {\'A}lvarez-Larena and Piniella, {J. Francesc}",

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T1 - Synthesis and characterization of a new chiral phosphinothiol ligand and its palladium(II) complexes

AU - Brugat, Nuria

AU - Duran, Josep

AU - Polo, Alfonso

AU - Real, Julio

AU - Álvarez-Larena, Ángel

AU - Piniella, J. Francesc

PY - 2002/4/19

Y1 - 2002/4/19

N2 - The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92% e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)4] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)2] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by 31P NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)2] gave the enantiomeric complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. © 2002 Elsevier Science Ltd. All rights reserved.

AB - The chiral ligand (1-diphenylphosphino-3-benzyloxy)propane-2-thiol 3 has been prepared both in racemic and enantiomerically enriched (92% e.e.) form. Addition of 2 equiv. of ligand 3 to a solution of [Pd(PPh3)4] gave the diastereoisomeric bischelate complexes [Pd(phosphinothiolato)2] 4 which exhibit a cis-trans equilibrium in solution. Formation of the diastereoisomeric complexes 4 allows the determination of the enantiomeric purity of ligand 3 by 31P NMR spectroscopy. Addition of 1 equiv. of ligand 3 to a solution of [PdCl2(PPh3)2] gave the enantiomeric complexes [PdCl(phosphinothiolate)(PPh3)] 5, which can be converted to the bischelate complexes 4 by addition of a second equivalent of ligand 3. This process allows the selective preparation of the two diastereoisomeric forms of complex 4. © 2002 Elsevier Science Ltd. All rights reserved.

U2 - 10.1016/S0957-4166(02)00143-X

DO - 10.1016/S0957-4166(02)00143-X

M3 - Article

VL - 13

SP - 569

EP - 577

IS - 6

ER -