Simple chiral diaminobinaphthyl dilithium salts for intramolecular catalytic asymmetric hydroamination of amino-1,3-dienes

Advanced Synthesis and Catalysis

Volumn 352, Issue 13, 2010, Pages 2171-2176

  Deschampa, Julia ^a   Olier, Clarisse ^a   Schulz, Emmanuelle ^a,b   Guillot, Régis ^b   Hannedouche, Jérôme ^a,b   Collin, Jacqueline ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

3 dienes; Amino l; Asymmetric catalysis; Hydroamination; Lithium; Nitrogen heterocycles

Indexed keywords

EID: 77956926277     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000302     Document Type: Article

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44. 1 was also an active catalyst for the enantioselective hydroamination of primary amines tethered to monosubstituted double bond, affording however the cyclised products with a lower level of enantioselectivity. For instance, under the catalytic conditions employed for substrate la, 3-methyl-2-azaspiro[4,5]decane was produced in 12% enantiomeric excess with a total conversion of the substrate in 4 h.
45. Attempts to directly observe a catalytic activity with these isolated racemic crystals were unsuccessful. Nevertheless, the addition of a catalytic amount of a MeLi solution to the so-obtained reaction media could restore similar activity and diastereoselectivity as those obtained with the lithium salts generated in situ under standard conditions (and different ones than those observed with MeLi alone).
46. 2=0.1331 (all data). See Supporting Information for more details,
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