Dibenzoylmethane → (S)-2-(1-(4-Chlorophenyl)-2-nitroethyl)-1,3-diphenylpropane-1,3-dione

HRID 1430768ノート

反応式

HRID 1430768 の反応式
[C:1]1([C:7](=[O:17])[CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[N+:27]([O-:29])=[O:28])=[CH:21][CH:20]=1>C(OCC)C>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C@H:25]([CH:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:17])[CH2:26][N+:27]([O-:29])=[O:28])=[CH:23][CH:24]=1

参加物

4

反応物 2

HCID 8433DibenzoylmethaneHCID 53541824-Chloro B-nitrostyrene

生成物 1

HCID 25212831(S)-2-(1-(4-Chlorophenyl)-2-nitroethyl)-1,3-diphenylpropane-1,3-dione

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
23 °C

実験手順

To a solution of 1,3-diphenyl-1,3-propanedione (1a) (0.3 mmol, 3 eq) and 1-chloro-4-((E)-2-nitrovinyl)benzene (2g) (0.1 mmol, 1 eq) in diethyl ether (0.3 mL) was added catalyst VI (Q-NH2) (0.015 mmol, 0.15 eq). The resulting mixture was stirred at room temperature (23° C.). After the reaction was complete (monitored by TLC), the product 3g was isolated and purified by centrifuge/washing with diethyl ether (0.3 mL). All the catalyst VI (0.15 equiv) and 2 equivalents of the excess the dione 1a were retained in the filtrate. The combined ethereal filtrate was evaporated to 0.3 mL before the dione 1a (1 eq) and 2g (1 eq) were added again to the solution for the next round of the Michael reaction. This was to ensure that the reaction condition for each cycle was almost the same as the previous one. The excellent yields (96% in average) and enantioselectivities (98-94% ee) were achieved in seven cycles.

出典と根拠

ORDレコード
ord-14f447125d0e457db89e368eb0076670
出典データセット
uspto-grants-2015_01
特許番号
US08940938B2

反応ノート

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