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Synthesis of Chiral Bisoxazoline Ligands: (3a R ,3a' R ,8a S ,8a' S )‐2,2'‐(Cyclopropane‐1,1‐Diyl)bis(3a,8a‐Dihydro‐8 H ‐Indeno[1,2‐
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Abstract
This chapter presents step by step procedure for the synthesis of chiral bisoxazoline ligands: (3aR,3a'R,8aS,8a'S)‐2,2'‐(cyclopropane‐1,1‐diyl)bis(3a,8a‐dihydro‐8H‐indeno[1,2‐d]oxazole). In 1996, Davies and coworkers at Merck Research Laboratories reported the synthesis of several bis(oxazoline) ligands from (1R,2S)‐1‐amino‐2,3‐dihydro‐1Hinden‐2‐ol, an intermediate in the synthesis of the HIV protease inhibitor Indinavir. Since these initial disclosures, (3aR,3a'R,8aS,8a'S)‐2,2'‐(cyclopropane‐1,1‐diyl)bis(3a,8adihydro‐8H‐indeno[1,2‐d]‐oxazole) has been used as a chiral ligand for numerous Lewis acidcatalyzed and transition metal‐catalyzed reactions. The wide range of transformations, under a variety of different modes of catalysis, demonstrates the utility of (3aR,3a'R,8aS,8a'S)‐2,2'‐(cyclopropane‐1,1‐diyl)bis(3a,8adihydro‐8H‐indeno[1,2‐d]‐oxazole) as a chiral ligand.
Title: Synthesis of Chiral Bisoxazoline Ligands: (3a
R
,3a'
R
,8a
S
,8a'
S
)‐2,2'‐(Cyclopropane‐1,1‐Diyl)bis(3a,8a‐Dihydro‐8
H
‐Indeno[1,2‐
Description:
Abstract
This chapter presents step by step procedure for the synthesis of chiral bisoxazoline ligands: (3aR,3a'R,8aS,8a'S)‐2,2'‐(cyclopropane‐1,1‐diyl)bis(3a,8a‐dihydro‐8H‐indeno[1,2‐d]oxazole).
In 1996, Davies and coworkers at Merck Research Laboratories reported the synthesis of several bis(oxazoline) ligands from (1R,2S)‐1‐amino‐2,3‐dihydro‐1Hinden‐2‐ol, an intermediate in the synthesis of the HIV protease inhibitor Indinavir.
Since these initial disclosures, (3aR,3a'R,8aS,8a'S)‐2,2'‐(cyclopropane‐1,1‐diyl)bis(3a,8adihydro‐8H‐indeno[1,2‐d]‐oxazole) has been used as a chiral ligand for numerous Lewis acidcatalyzed and transition metal‐catalyzed reactions.
The wide range of transformations, under a variety of different modes of catalysis, demonstrates the utility of (3aR,3a'R,8aS,8a'S)‐2,2'‐(cyclopropane‐1,1‐diyl)bis(3a,8adihydro‐8H‐indeno[1,2‐d]‐oxazole) as a chiral ligand.
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