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912956

Sigma-Aldrich

(2R,2′R,3R,3′R)-MeO-BIBOP

Synonym(s):

(2R,2′R,3R,3′R)-3,3′-Di-tert-butyl-4,4′-dimethoxy-2,2′,3,3′-tetrahydro-2,2′-bibenzo[d][1,3]oxaphosphole

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About This Item

Empirical Formula (Hill Notation):
C24H32O4P2
CAS Number:
1228758-57-3
Molecular Weight:
446.46
UNSPSC Code:
12352200
NACRES:
NA.22

form

powder

Quality Level

100

optical purity

ee: ≥99% (HPLC)

reaction suitability

reagent type: ligand

functional group

phosphine

Related Categories

Application

(2R,2′R,3R,3′R)-MeO-BIBOP is a P-chiral biphosphorus ligand used in a variety of asymmetric transition metal-catalyzed transformations including hydrogenations, propargylations, reductions, and hydroformylations.

Product can be used with our benchtop hydrogen generator, H-Genie Lite (Z744083)

Other Notes

Copper Catalyzed Asymmetric Propargylation of Aldehydes

Legal Information

Sold in collaboration with Zejun Pharmaceuticals

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

912956-250MG:
912956-VAR:
912956-100MG:
912956-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Daniel R Fandrick et al.
Journal of the American Chemical Society, 132(22), 7600-7601 (2010-05-21)
The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of the TMS
Renchang Tan et al.
Organic letters, 18(14), 3346-3349 (2016-06-23)
Air-stable and tunable chiral bisdihydrobenzooxaphosphole ligands (BIBOPs) were employed in rhodium-catalyzed asymmetric hydroformylation of various terminal olefins with excellent conversions (>99%), moderate-to-excellent enantioselectivities (up to 95:5 er), and branched to linear ratios (b:l) of up to 400.
Chengxi Li et al.
Angewandte Chemie (International ed. in English), 58(38), 13573-13583 (2019-07-26)
We herein report the development of a conformationally defined, electron-rich, C2 -symmetric, P-chiral bisphosphorus ligand, ArcPhos, by taking advantage of stereoelectronic effects in ligand design. With the Rh-ArcPhos catalyst, excellent enantioselectivities and unprecedentedly high turnovers (TON up to 10 000) were

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