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685232

Bis[(R,R,S)-DiazaPhos-SPE]

Name: Bis[(R,R,S)-DiazaPhos-SPE]
Brand: ALDRICH

Synonym(s):

2,2′,2″,2′′′-(1,2-Phenylenebis[(1R,3R)-tetrahydro-5,8-dioxo-1H-[1,2,4]diazaphospholo[1,2-a]pyridazine-2,1,3(3H)-triyl])tetrakis(N-[(1S)-1-phenylethyl])benzamide

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About This Item

Empirical Formula (Hill Notation):

C₇₈H₇₂N₈O₈P₂

CAS Number:

851609-33-1

Molecular Weight:

1311.40

UNSPSC Code:

12352005

PubChem Substance ID:

329760953

optical activity

[α]20/D -82.0°, c = 1 in THF

mp

183-195 °C

SMILES string

C[C@H](NC(=O)c1ccccc1[C@H]2N3N([C@H](P2c4ccccc4P5[C@@H](N6N([C@H]5c7ccccc7C(=O)N[C@@H](C)c8ccccc8)C(=O)CCC6=O)c9ccccc9C(=O)N[C@@H](C)c%10ccccc%10)c%11ccccc%11C(=O)N[C@@H](C)c%12ccccc%12)C(=O)CCC3=O)c%13ccccc%13

InChI

1S/C78H72N8O8P2/c1-49(53-27-9-5-10-28-53)79-71(91)57-35-17-21-39-61(57)75-83-67(87)45-46-68(88)84(83)76(62-40-22-18-36-58(62)72(92)80-50(2)54-29-11-6-12-30-54)95(75)65-43-25-26-44-66(65)96-77(63-41-23-19-37-59(63)73(93)81-51(3)55-31-13-7-14-32-55)85-69(89)47-48-70(90)86(85)78(96)64-42-24-20-38-60(64)74(94)82-52(4)56-33-15-8-16-34-56/h5-44,49-52,75-78H,45-48H2,1-4H3,(H,79,91)(H,80,92)(H,81,93)(H,82,94)/t49-,50-,51-,52-,75+,76+,77+,78?,96?/m0/s1

InChI key

NTWCWWNZWYJTEP-GEDBLHTESA-N

Application

Diazaphospholane Ligands for Catalytic Asymmetric Transformations

Catalyst for:

Enantioselective synthesis of α,β-unsaturated aldehydes via hydroformylation of dienes
Regioselective and enantioselective hydroformylation of dialkyl acrylamides
Asymmetric hydroformylation of vinyl acetate
Regioselective and stereoselective hydroformylation of alkenes

Diazaphospholane ligands display excellent levels of conversion and selectivity in Rh-catalyzed asymmetric hydroformylation reactions.

Legal Information

Product is sold for R&D purpose only and use by end user in the manufacture of products of commerce is not permitted. Product is sold in association with Dowpharma^SM a business unit of The Dow Chemical Company. U.S. Pat. 7,071,357B.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Highly active, regioselective, and enantioselective hydroformylation with Rh catalysts ligated by Bis-3,4-diazaphospholanes.

Thomas P Clark et al.

Journal of the American Chemical Society, 127(14), 5040-5042 (2005-04-07)

Azines made by the reaction of hydrazine with ortho-formylbenzoic acid react with 1,2-diphosphinobenzene and either succinyl chloride or phthaloyl chloride in ca. 30% yield to give rac-bis-3,4-diazaphospholanes bearing benzoic acid groups in the 2 and 5 positions. Condensation of the

Highly regio- and enantioselective asymmetric hydroformylation of olefins mediated by 2,5-disubstituted phospholane ligands.

Alex T Axtell et al.

Angewandte Chemie (International ed. in English), 44(36), 5834-5838 (2005-08-13)

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