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650889

Sigma-Aldrich

(S,S′,R,R′)-TangPhos

Synonym(s):

(1S,1S′,2R,2R′)-1,1′-Di-tert-butyl-(2,2′)-diphospholane

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About This Item

Empirical Formula (Hill Notation):
C16H32P2
CAS Number:
470480-32-1
Molecular Weight:
286.37
UNSPSC Code:
12352005
PubChem Substance ID:
24883788

mp

60-65 °C

SMILES string

CC(C)(C)P1CCC[C@@H]1[C@H]2CCCP2C(C)(C)C

InChI

1S/C16H32P2/c1-15(2,3)17-11-7-9-13(17)14-10-8-12-18(14)16(4,5)6/h13-14H,7-12H2,1-6H3/t13-,14-,17+,18+/m1/s1

InChI key

SJNUZTRUIDRSJK-KNCCTNLNSA-N

Application

Chiral Quest Phosphine Ligands for Asymmetric Hydrogenation

Catalytic ligand used in:
  • Preparation of α-borono-substituted alkylarenes by asymmetric hydroboration of styrenes catalyzed by copper(I)
  • Enantioselective synthesis of spiroindane di-Me acetic acid via hydrogenation of spiroindane di-Me acetic acid catalyzed by Ru(II)
  • Asymmetric γ-addition of thiols to allenoates
  • Rhodium-catalyzed intermolecular enantioselective hydroacylation of alkynes to give alpha- and beta-substituted unsaturated ketones by kinetic resolution
  • Stereoselective preparation of β-amino nitriles via rhodium-catalyzed asymmetric hydrogenation of amino acrylonitriles
Highly efficient in rhodium-catalyzed hydrogenation of α-dehyroamino acids and α-arylenamides,[1] β-(acylamino)acrylates,[2] itaconic acids, and enol acetates.[3] Also gives outstanding enantioselectivities in asymmetric hydroformylation reactions.[4]

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP5014V
MKBJ3489V
MKBH0023V
02345ED
02245ED

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Wenjun Tang et al.
Organic letters, 4(23), 4159-4161 (2002-11-09)
The Rh-TangPhos complex is an efficient hydrogenation catalyst for making chiral beta-amino acid derivatives. With the Rh-TangPhos system, high enantioselectivities (up to 99.6%) and turnover numbers have been obtained in the hydrogenation of E/Z isomeric mixtures of both beta-alkyl and
Wenjun Tang et al.
Organic letters, 5(2), 205-207 (2003-01-17)
[reaction: see text] The Rh-TangPhos catalyst has been used for asymmetric hydrogenation of itaconic acid and enol acetate derivatives. A variety of chiral 2-substituted succinic acids and chiral acetates have been obtained in excellent ee values (up to 99% ee).
Axtell, A. T. et al.
Organometallics, 25, 5003-5003 (2006)
A chiral 1,2-bisphospholane ligand with a novel structural motif: applications in highly enantioselective Rh-catalyzed hydrogenations.
Wenjun Tang et al.
Angewandte Chemie (International ed. in English), 41(9), 1612-1614 (2002-05-03)

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