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700746

Sigma-Aldrich

(S)-SDP

≥95%

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Synonym(s):
(S)-(−)-7,7′-Bis(diphenylphosphino)-2,2′,3,3′-tetrahydro-1,1′-spirobiindene, (S)-7,7′-Bis(diphenylphosphino)-1,1′-spirobiindane
Empirical Formula (Hill Notation):
C41H34P2
CAS Number:
Molecular Weight:
588.66
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥95%

form

solid

optical activity

[α]22/D −191°, c = 1 in chloroform

mp

199-204 °C

storage temp.

−20°C

SMILES string

C1CC2(CCc3cccc(P(c4ccccc4)c5ccccc5)c23)c6c1cccc6P(c7ccccc7)c8ccccc8

InChI

1S/C41H34P2/c1-5-17-33(18-6-1)42(34-19-7-2-8-20-34)37-25-13-15-31-27-29-41(39(31)37)30-28-32-16-14-26-38(40(32)41)43(35-21-9-3-10-22-35)36-23-11-4-12-24-36/h1-26H,27-30H2

InChI key

DKZNVWNOOLQCMJ-UHFFFAOYSA-N

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This Item
70075470085176854
(S)-SDP ≥95%

700746

(S)-SDP

(R)-SDP

700754

(R)-SDP

(S)-Xyl-SDP

700851

(S)-Xyl-SDP

form

solid

form

solid

form

solid

form

crystals

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

mp

199-204 °C

mp

198-203 °C

mp

>300 °C

mp

-

optical activity

[α]22/D −191°, c = 1 in chloroform

optical activity

[α]22/D +184°, c = 1 in chloroform

optical activity

[α]22/D −62.0°, c = 1 in chloroform

optical activity

[α]20/D −59.0±4°, c = 1% in chloroform

General description

(S)-SDP is a chiral diphosphine reagent used in the asymmetric hydrogenation of ketones catalyzed by transition metal. It is also used in hydrosilylation or cyclization of 1,6-enynes.

Application

(S)-SDP can be used:
  • As a ligand in the ruthenium-catalyzed asymmetric hydrogenation of cyclic ketones to give cycloalkanols.
  • To prepare ruthenium complexes, which are used in the asymmetric hydrogenation of different prochiral ketones.

related product

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Description
Pricing

Storage Class

11 - 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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(R?and (S)?7,7′?Bis(diphenylphosphino)?2,2′,3,3′?tetrahydro?1,1′?spirobiindene
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2008)
Synthesis of spiro diphosphines and their application in asymmetric hydrogenation of ketones
Xie J, et al.
Journal of the American Chemical Society, 125(15), 4404-4405 (2003)
Dynamic Kinetic Resolution Allows a Highly Enantioselective Synthesis of cis-alpha-Aminocycloalkanols by Ruthenium-Catalyzed Asymmetric Hydrogenation
Liu S, et al.
Angewandte Chemie (International ed. in English), 46(39), 7506-7508 (2007)

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