Asymmetric deprotonation of N -boc piperidine: React IR monitoring and mechanistic aspects

Journal of the American Chemical Society

Volumn 132, Issue 21, 2010, Pages 7260-7261

  Stead, Darren ^a   Carbone, Giorgio ^a   O'Brien, Peter ^a   Campos, Kevin R ^b   Coldham, Iain ^c   Sanderson, Adam ^d  

^a UNIVERSITY OF YORK   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

^c UNIVERSITY OF SHEFFIELD   (United Kingdom)

^d ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT OBSERVATION; IN-SITU; LITHIATION; MECHANISTIC ASPECTS; PRE-LITHIATION;

PIPERIDINE DERIVATIVE;

ARTICLE; INFRARED SPECTROSCOPY; LITHIATION; MONITORING; QUANTUM YIELD; REACTION ANALYSIS; STEREOSPECIFICITY;

PIPERIDINES; PROTONS; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 77952804275     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102043e     Document Type: Article

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21. A similar rationale has been noted for a related 6-ring N -Boc heterocycle (see ref 4b) and can explain the low er previously obtained by us in the lithiation trapping of N -Boc piperidine 1 using 1.4 equiv of s -BuLi and 2.4 equiv of (+)-sparteine surrogate 5 (see ref 7 and SI).
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