Amine Protection/α-Activation with the tert-Butoxythiocarbonyl Group: Application to Azetidine Lithiation–Electrophilic Substitution

tert-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on N-Botc-azetidine. N,N,N′,N′-endo,endo-Tetramethyl-2,5-diaminonorbornane proved optimal as a chiral ligand, generating adducts...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 2; pp. 330 - 333
Main Authors Hodgson, David M, Mortimer, Claire L, McKenna, Jeffrey M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.01.2015
Amer Chemical Soc
Subjects
Amines - chemistry
Azetidines - chemistry
Chemistry
Chemistry, Organic
Diamines - chemistry
Formic Acid Esters - chemistry
Lithium - chemistry
Molecular Structure
Norbornanes - chemistry
Organometallic Compounds - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
FUNCTIONALIZATION
ARYL
DERIVATIVES
CYCLIC AMINES
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Summary:tert-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on N-Botc-azetidine. N,N,N′,N′-endo,endo-Tetramethyl-2,5-diaminonorbornane proved optimal as a chiral ligand, generating adducts with er up to 92:8. Facile deprotection, under conditions that left the corresponding N-Boc systems intact, was achieved using either TFA or via thermolysis in ethanol.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol503441d