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912727

(2R,3R)-iPr-BIDIME

Name: (2<I>R</I>,3<I>R</I>)-iPr-BIDIME
Brand: ALDRICH

Synonym(s):

(2R,3R)-3-(Tert-butyl)-4-(2,6-dimethoxyphenyl)-2-isopropyl-2,3-dihydrobenzo[d][1,3]oxaphosphole

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₉O₃P

CAS Number:

1477517-19-3

Molecular Weight:

372.44

MDL number:

MFCD31630762

UNSPSC Code:

12352200

NACRES:

NA.22

Form:

powder and chunks

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Properties

form

powder and chunks

Quality Level

100

optical purity

ee: ≥99% (HPLC)

reaction suitability

reagent type: ligand

functional group

phosphine

SMILES string

P1([C@@H](Oc2c1c(ccc2)c3c(cccc3OC)OC)C(C)C)C(C)(C)C

InChI

1S/C22H29O3P/c1-14(2)21-25-18-13-8-10-15(20(18)26(21)22(3,4)5)19-16(23-6)11-9-12-17(19)24-7/h8-14,21H,1-7H3/t21-,26?/m1/s1

InChI key

AVUPKIFOTAYCAC-OSMGYRLQSA-N

Description

Application

(2R,3R)-iPr-BIDIME is a P-chiral monophosphorus ligand used for the transition metal-catalyzed asymmetric Suzuki-Miyaura and hydroboration reactions.

Other Notes

Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides

Legal Information

Sold in collaboration with Zejun Pharmaceuticals

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

MKCT9579

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Efficient syntheses of korupensamines A, B and michellamine B by asymmetric Suzuki-Miyaura coupling reactions.

Guangqing Xu et al.

Journal of the American Chemical Society, 136(2), 570-573 (2013-10-24)

Efficient asymmetric Suzuki-Miyaura coupling reactions are employed for the first time in total syntheses of chiral biaryl natural products korupensamine A and B in combination with an effective diastereoselective hydrogenation, allowing ultimately a concise and stereoselective synthesis of michellamine B.

Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides.

Naifu Hu et al.

Journal of the American Chemical Society, 137(21), 6746-6749 (2015-05-06)

The rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).

Global Trade Item Number

SKU	GTIN
912727-50MG	04061841874010
912727-250MG	04061841874003