Synthesis of a trans-chelating chiral diphosphine ligand with only planar chirality and its application to asymmetric hydrosilylation of ketones

R. Kuwano, T. Uemura, M. Saitoh, Y. Ito

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

Optically active diphosphine (S,S)-2,2-bis[(diethylphosphino)methyl]- 1,1-biferrocene (abbreviated to (S,S)-EtTRAP-H) was synthesized from ferrocenyloxazoline derived from-L-valinol in 47% overall yield. The new chiral ligand, (S,S)-EtTRAP-H, which coordinates to a rhodium atom in a trans-chelating manner, was effective for asymmetric hydrosilylation of ketones to give optically active secondary alcohols with up to 94% ee.

Original languageEnglish
Pages (from-to)1327-1330
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number7
DOIs
Publication statusPublished - Feb 12 1999
Externally publishedYes

Fingerprint

Hydrosilylation
Rhodium
Chirality
Chelation
Ketones
Alcohols
Ligands
Atoms
valinol

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Synthesis of a trans-chelating chiral diphosphine ligand with only planar chirality and its application to asymmetric hydrosilylation of ketones. / Kuwano, R.; Uemura, T.; Saitoh, M.; Ito, Y.

In: Tetrahedron Letters, Vol. 40, No. 7, 12.02.1999, p. 1327-1330.

Research output: Contribution to journalArticle

@article{1a2ac25815434d5cb20fde25142a4f04,
title = "Synthesis of a trans-chelating chiral diphosphine ligand with only planar chirality and its application to asymmetric hydrosilylation of ketones",
abstract = "Optically active diphosphine (S,S)-2,2-bis[(diethylphosphino)methyl]- 1,1-biferrocene (abbreviated to (S,S)-EtTRAP-H) was synthesized from ferrocenyloxazoline derived from-L-valinol in 47{\%} overall yield. The new chiral ligand, (S,S)-EtTRAP-H, which coordinates to a rhodium atom in a trans-chelating manner, was effective for asymmetric hydrosilylation of ketones to give optically active secondary alcohols with up to 94{\%} ee.",
author = "R. Kuwano and T. Uemura and M. Saitoh and Y. Ito",
year = "1999",
month = "2",
day = "12",
doi = "10.1016/S0040-4039(98)02603-3",
language = "English",
volume = "40",
pages = "1327--1330",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "7",

}

TY - JOUR

T1 - Synthesis of a trans-chelating chiral diphosphine ligand with only planar chirality and its application to asymmetric hydrosilylation of ketones

AU - Kuwano, R.

AU - Uemura, T.

AU - Saitoh, M.

AU - Ito, Y.

PY - 1999/2/12

Y1 - 1999/2/12

N2 - Optically active diphosphine (S,S)-2,2-bis[(diethylphosphino)methyl]- 1,1-biferrocene (abbreviated to (S,S)-EtTRAP-H) was synthesized from ferrocenyloxazoline derived from-L-valinol in 47% overall yield. The new chiral ligand, (S,S)-EtTRAP-H, which coordinates to a rhodium atom in a trans-chelating manner, was effective for asymmetric hydrosilylation of ketones to give optically active secondary alcohols with up to 94% ee.

AB - Optically active diphosphine (S,S)-2,2-bis[(diethylphosphino)methyl]- 1,1-biferrocene (abbreviated to (S,S)-EtTRAP-H) was synthesized from ferrocenyloxazoline derived from-L-valinol in 47% overall yield. The new chiral ligand, (S,S)-EtTRAP-H, which coordinates to a rhodium atom in a trans-chelating manner, was effective for asymmetric hydrosilylation of ketones to give optically active secondary alcohols with up to 94% ee.

UR - http://www.scopus.com/inward/record.url?scp=0033547994&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033547994&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)02603-3

DO - 10.1016/S0040-4039(98)02603-3

M3 - Article

AN - SCOPUS:0033547994

VL - 40

SP - 1327

EP - 1330

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 7

ER -