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Technology Spotlight

MeOBIPHEP

 
Introduction

State-of-the-art atropisomeric MeOBIPHEP ligands, also referred to as MeO-BIPHEP, originally developed by Roche, have an extraordinarily broad performance profile for many synthetic applications due to their modular ligand design. In many respects, the catalytic profile of the MeOBIPHEP ligands is rather similar to that of other atropisomeric diphosphines such as BINAP and its many analogs.1–4 The nature of the PR2 group strongly influences the catalytic performance of the metal complexes, and the ligands available in research quantities from Sigma-Aldrich represent examples with different steric bulk.

 
References:
  1. Mordant, C. et al. Synthesis 2003, 2405.
  2. Wang, W.-B. et al. J. Am. Chem. Soc. 2003, 125, 10536.
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C–C coupling reactions

The Krische group reported on the enantioselective Rh-catalyzed reductive coupling of acetylene to aldehydes to α-ketoesters using 29510 to yield the corresponding diene alcohols in good yields and enantioselectivities (1st eq.). The Wiedenhoefer group reported on the intramolecular asymmetric hydroarylation of 2-(4-pentenyl)indoles in moderate to good yield with up to 90% ee catalyzed by a 1:1 mixture of dichloro platinum complex and (S)-3,5-t-Bu-4-MeO-MeOBIPHEP 29511 (2nd eq.). Pregosin and co-workers reported a dramatic improvement of enantioselection in the Pd-catalyzed Heck reaction of aryl triflates to 2-substituted dihydrofuranes when using (R)-3,5-t-Bu-MeOBIPHEP 29524 (3rd eq.).

 
 

MeOBIPHEP Scheme 4 Image

Scheme 4

References
  1. Tschoerner, M. et al. Organometallics 1999, 18, 670.
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Product No. Product Name Structure Add to Cart
29510 (R)-(+)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) 29510 Structure Image
29511 (S)-(-)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) 29511 Structure Image
29512 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine] 29512 Structure Image
29513 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine] 29513 Structure Image
29514 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(di-2-furylphosphine) 29514 Structure Image
29515 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(di-2-furylphosphine) 29515 Structure Image
29516 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-dimethylphenyl)phosphine] 29516 Structure Image
29517 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-dimethylphenyl)phosphine] 29517 Structure Image
29518 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine) 29518 Structure Image
29519 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diisopropylphosphine) 29519 Structure Image
29520 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(4-methylphenyl)phosphine] 29520 Structure Image
29521 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(4-methylphenyl)phosphine] 29521 Structure Image
29524 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] 29524 Structure Image
29525 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,5-di-tert-butylphenyl)phosphine] 29525 Structure Image
29526 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine] 29526 Structure Image
29527 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis[bis(3,4,5-trimethoxyphenyl)phosphine] 29527 Structure Image
29528 (R)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis{bis[3,5-diisopropyl-4-(dimethylamino)phenyl]phosphine} 29528 Structure Image
29529 (S)-(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis{bis[3,5-diisopropyl-4-(dimethylamino)phenyl]phosphine} 29529 Structure Image
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