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May 5, 2003
Volume 81, Number 18
CENEAR 81 18 p. 52
ISSN 0009-2347
CONTEST

Vying For Chiral Hydroformylation Advantage

Hydroformylation of unsaturated nitriles has been attracting the attention of researchers at DSM and Dowpharma. Last month, DSM chemists Johannes G. de Vries and Mariëlle M. H. Lambers-Verstappen reported the asymmetric hydroformylation of allyl cyanide using a rhodium-BINAPHOS complex [Adv. Synth. Catal., 345, 478 (2003)]. Also last month, at a conference in the Netherlands, Dowpharma chemist Paul Moran described an even better catalyst.

Hydroformylation of allyl cyanide is an atom-economical route to 2-methyl-3-cyanopropanal. Hydrogenation converts this aldehyde to 2-methyl-4-aminobutanol. (R)-2-Methyl-4-aminobutanol is a building block for TAK-637, a compound being developed by Takeda Chemical Industries for urinary continence. The compound is in Phase I clinical trials.

So far, asymmetric hydroformylation of substrates other than styrenes is relatively undeveloped. The rhodium-BINAPHOS complex converts allyl cyanide to the aldehyde in 66% enantiomeric excess. Dowpharma's new ligand achieves 80% ee and a far superior branched-to-linear ratio of 23:1 compared with 3:1 for BINAPHOS.

The new ligand, called Kelliphite, is a variation of Chiraphite, a ligand that has been used by Dow Chemical to hydroformylate styrenes. "Much of the reported work was carried out on styrene, and it wasn't that exciting," says Ian C. Lennon, a technology leader at Dowpharma. "We felt that if it we could expand the range of substrates and get new catalysts based on screening, we could have offerings here."

Dowpharma has demonstrated reduction of the chiral aldehyde to the TAK-637 amino alcohol building block. "Obviously, we hope Takeda and others will be interested in our process," Lennon says.


COVER STORY
CHIRAL BUSINESS
Fine chemicals companies are jockeying for position to deliver the increasingly complicated chiral small molecules of the future

CONTEST
Vying For Chiral Hydroformylation Advantage

NICHE PLAYER
Chiral Quest Sees Advantages In Independence

STEADY SHARE
Worldwide sales of single-enantiomer pharmaceutical products approach $160 billion

BLOCKBUSTERS
Top 10 single-enantiomer products belong to billion-dollar club

CHIRALITY AT WORK
Drug developers can learn much from recent successful and failed chiral switches

REALITY CHECK
When Chemistry Bows To Economics

HARVEST
Research in Chiral Fine Chemicals Reaps Recognition

CONSTANT
Chiral separations are enduring items in the toolbox

CASE HISTORIES
History and choice shape portfolios

CALENDAR
Events Of Interest





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Chemical & Engineering News
Copyright © 2003 American Chemical Society



 
Visit SGI
COVER STORY
CHIRAL BUSINESS
Fine chemicals companies are jockeying for position to deliver the increasingly complicated chiral small molecules of the future

CONTEST
Vying For Chiral Hydroformylation Advantage

NICHE PLAYER
Chiral Quest Sees Advantages In Independence

STEADY SHARE
Worldwide sales of single-enantiomer pharmaceutical products approach $160 billion

BLOCKBUSTERS
Top 10 single-enantiomer products belong to billion-dollar club

CHIRALITY AT WORK
Drug developers can learn much from recent successful and failed chiral switches

REALITY CHECK
When Chemistry Bows To Economics

HARVEST
Research in Chiral Fine Chemicals Reaps Recognition

CONSTANT
Chiral separations are enduring items in the toolbox

CASE HISTORIES
History and choice shape portfolios

CALENDAR
Events Of Interest


Related Stories
Custom Chemicals
[C&EN, Feb. 17, 2003]

Pharma Business
[C&EN, Jan. 27, 2003]

Fine Chemicals
[C&EN, July 22, 2002]

Chiral Chemistry
[C&EN, Jun. 10, 2002]

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