Stereoselective synthesis of cyclopropane rings under phase-transfer- catalyzed conditions

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9572-9575

  Arai, Shigeru ^a   Nakayama, Keiji ^a   Hatano, Kei Ichiro ^a   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032509497     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981409y     Document Type: Article

References (31)

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23. No other products except 3a were detected on TLC in these reaction systems.
24. Other PTCs involving an aromatic ring or a longer hydrophobic chain such as benzyltriethylammonium bromide (BTEB) or decyltrimethylammonium bromide (DTMB) are less effective in this reaction system.
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29. 1H NMR analysis of the above-mentioned compounds, the stereochemistry of other cyclopropanated products were assigned.
30. No isomerization occurred with compound 5b under similar reaction conditions. Treatment of 6 with DBU resulted in decomposition of the starting materials.
31. According to thermodynamic calculation for four possible diastereomers of cyclopropane derivatives using MOPAC 93 Rev.2-AM1, the isomer obtained was found not to be the most stable one, which has an energy gap of 1.92 kcal/mol relative to the most stable isomer. The reason for this unique stereoselectivity in this cyclopropanation reaction is not presently clear, though it seems that the stereocontrol in this reaction is not strongly dependent on the thermodynamic stability of the products but on kinetic factors during the cyclization step.