Textbook Question
Identify the alkene that would react with Ti(OiPr)₄, (+) -diethyltartrate, and t-butylhydroperoxide to give the following chiral, nonracemic epoxides.
(c)
602
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Ch. 9 - Alkenes II: Oxidation and Reduction
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 8, Problem 41
The chiral catalyst (R)-BINAP(COD)RhOTf was used in a hydrogenation reaction as part of the synthesis of fragment C of indinavir. Using the same alkene, predict the product that would be obtained if (S)-BINAP(COD)RhOTf were used instead.
Verified step by step guidance1
Identify the role of the chiral catalyst in the reaction. In this case, (R)-BINAP(COD)RhOTf is used to induce chirality in the hydrogenation of an alkene, leading to a specific enantiomer of the product.
Understand the concept of enantiomers. Enantiomers are pairs of molecules that are mirror images of each other and cannot be superimposed. The use of a chiral catalyst can lead to the formation of one enantiomer preferentially over the other.
Recognize that (S)-BINAP(COD)RhOTf is the enantiomer of (R)-BINAP(COD)RhOTf. This means that using (S)-BINAP(COD)RhOTf will favor the formation of the opposite enantiomer of the product compared to using (R)-BINAP(COD)RhOTf.
Predict the stereochemistry of the product. Since (R)-BINAP(COD)RhOTf leads to one enantiomer, using (S)-BINAP(COD)RhOTf will result in the formation of the enantiomeric product with the opposite configuration at the chiral center.
Consider the implications of this change in stereochemistry for the synthesis of fragment C of indinavir. The stereochemistry of the product is crucial for the biological activity of the final compound, so using the correct enantiomer of the catalyst is essential for the desired outcome.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Chirality in Catalysts
Chirality refers to the geometric property where a molecule is not superimposable on its mirror image, much like left and right hands. In catalysis, chiral catalysts can induce stereoselectivity, leading to the preferential formation of one enantiomer over another in a chemical reaction. This is crucial in synthesizing compounds with specific desired properties, such as pharmaceuticals.
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Nucleophilic Catalysis Concept 1
Enantioselective Hydrogenation
Enantioselective hydrogenation is a process where a chiral catalyst is used to selectively hydrogenate one enantiomer of an unsaturated compound over the other. This reaction is important in producing enantiomerically pure compounds, which are often required in drug synthesis. The choice of catalyst, such as (R)-BINAP or (S)-BINAP, determines the stereochemistry of the product.
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Guided course
00:48The definition of hydrogenation.
Role of BINAP in Catalysis
BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) is a chiral ligand used in asymmetric catalysis. It forms complexes with metals like Rhodium, which can then catalyze reactions with high enantioselectivity. The (R) or (S) configuration of BINAP influences the spatial arrangement of the reactants, thus determining the stereochemistry of the hydrogenation product.
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2:31Nucleophilic Catalysis Concept 1
Related Practice
Textbook Question
Calculate the oxidation number for the indicated carbons.
(c)
1224
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Textbook Question
Calculate the oxidation number for the indicated carbons.
(b)
1327
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Textbook Question
Calculate the oxidation number for the indicated carbons.
(a)
1412
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Textbook Question
Identify the alkene that would react with Ti(OiPr)₄, (+) -diethyltartrate, and t-butylhydroperoxide to give the following chiral, nonracemic epoxides.
(a)
861
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Textbook Question
Identify the alkene that would react with Ti(OiPr)4, (+) -diethyltartrate, and t-butylhydroperoxide to give the following chiral, nonracemic epoxides.
(b)
585
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