Enantiomerically pure 2-bromo-2′-diphenylphosphinyl-1,1′- binaphthyl as a monophosphorus template for electrophilic functionalization in chiral MOP-type ligand synthesis

Journal of Organic Chemistry

Volumn 70, Issue 22, 2005, Pages 9085-9087

  Hoshi, Takashi ^a   Hayakawa, Tetsuji ^a   Suzuki, Toshio ^a   Hagiwara, Hisahiro ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; IODINE; PALLADIUM; SYNTHESIS (CHEMICAL);

ELECTROPHILIC FUNCTIONALIZATION; LITHIATION; MONOPHOSPHINYLATION; MONOPHOSPHORUS TEMPLATE;

ORGANOMETALLICS;

2 BROMO 2' DIPHENYLPHOSPHINYL 1,1' BINAPHTHYL; LIGAND; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CHEMICAL REACTION; CHEMOSENSITIVITY; CHIRALITY; ENANTIOMER; LITHIATION; REACTION ANALYSIS; SULFENYLATION;

EID: 27444444500     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051581j     Document Type: Article

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29. We also observed the drastic decrease in enantiopurity of the sulfenylation product 5b when the standard sulfenylation procedure was carried out in which lithiation of 2a was followed by substitution of the resultant 4 with p-tolyl p-toluenethiosulfonate. See the Supporting Information for details.
30. In the lithiation of 2a. the use of MeLi is essential for the selective cleavage of the C-Br bond to generate the intermediate 4. When more reactive n-BuLi was used as a lithiation reagent, the cleavage of the C-P bond also took place. The weak nucleophilicity of MeLi is also an important element of the in situ lithiation of 2a in the presence of the highly electrophilic thiosulfonate.