Synthesis of Ramirez ylides from Morita-Baylis-Hillman adducts of α-bromocinnamaldehyde: an intramolecular 1,6-conjugate addition of phosphorus ylide

被引:8
作者
Kim, Ko Hoon [1 ,2 ]
Lee, Sangku [3 ]
Lee, Junseong [1 ,2 ]
Kim, Jae Nyoung [1 ,2 ]
机构
[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea
[2] Chonnam Natl Univ, Inst Basic Sci, Kwangju 500757, South Korea
[3] Korea Res Inst Biosci & Biotechnol, Targeted Med Res Ctr, Cheongwon 363883, Chungbuk, South Korea
基金
新加坡国家研究基金会;
关键词
Ramirez ylides; Morita-Baylis-Hillman adducts; Phosphines; Intramolecular 1,6-conjugate addition; EFFICIENT SYNTHESIS; WITTIG OLEFINATION; ASSISTED SYNTHESIS; PHOSPHINE; COMPLEXES; 1-C9H6PMEPH2; CONSTRUCTION; 1,6-ADDITION; CYCLIZATION; CARBONATES;
D O I
10.1016/j.tetlet.2015.05.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ramirez ylides were synthesized in good yields from Morita-Baylis-Hillman acetates of alpha-bromocin-namaldehyde and phosphines in a one-pot reaction. The Ramirez ylides were formed by a novel intramolecular 1,6-conjugate addition of phosphorus ylide as a key step. (c) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4349 / 4353
页数:5
相关论文
共 57 条
[31]   An efficient synthesis of o-terphenyls from Morita-Baylis-Hillman adducts of cinnamaldehydes: a consecutive bromination, Wittig reaction, 6π-electrocyclization, and an aerobic oxidation process [J].
Lim, Cheol Hee ;
Kim, Sung Hwan ;
Kim, Ko Hoon ;
Kim, Jae Nyoung .
TETRAHEDRON LETTERS, 2013, 54 (20) :2476-2479
[32]   Organocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters [J].
Lin, Aijun ;
Wang, Junying ;
Mao, Haibin ;
Ge, Huiming ;
Tan, Renxiang ;
Zhu, Chengjian ;
Cheng, Yixiang .
ORGANIC LETTERS, 2011, 13 (16) :4176-4179
[33]   Substrate-Controlled, Phosphine-Catalyzed Domino Reactions of Activated Conjugated Dienes: Highly Diastereoselective Synthesis of Bicyclic Skeletons [J].
Ma, Jianze ;
Xie, Peizhong ;
Hu, Chongchong ;
Huang, You ;
Chen, Ruyu .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (27) :7418-7422
[34]   Microwave-assisted synthesis of the (E)-a-methylalkenoate framework from multifunctionalized allylic phosphonium salts [J].
Meier, Lidiane ;
Ferreira, Misael ;
Sa, Marcus M. .
HETEROATOM CHEMISTRY, 2012, 23 (02) :179-186
[35]   Synthesis of 3-(γ, δ-Disubstituted)allylidene-2-Oxindoles from Isatins by Wittig Reaction with Morita-Baylis-Hillman Bromides [J].
Moon, Hye Ran ;
Kim, Ko Hoon ;
Lee, Junseong ;
Kim, Jae Nyoung .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01) :219-225
[36]   A novel three-component reaction of triphenylphosphine, DMAD, and electron-deficient styrenes: Facile synthesis of cyclopentenyl phosphoranes [J].
Nair, V ;
Deepthi, A ;
Beneesh, PB ;
Eringathodi, S .
SYNTHESIS-STUTTGART, 2006, (09) :1443-1446
[37]   Intramolecular 1,6-conjugate addition approach for construction of the hydrindane framework: Total synthesis of (+/-)-coronafacic acid [J].
Nara, S ;
Toshima, H ;
Ichihara, A .
TETRAHEDRON LETTERS, 1996, 37 (37) :6745-6748
[38]   Product diversity in the reaction of [(norbornadiene){CpP(iPr)2}Rh with alkyl iodides [J].
Ortega, Esteban ;
Kleigrewe, Nina ;
Kehr, Gerald ;
Erker, Gerhard ;
Froehlich, Roland .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, (18) :3769-3774
[39]   Discovery and Synthetic Value of a Novel, Highly Crowded Cyclopentadienylphosphane Ph2P-Cp™H and Its Ferrocenyl-Bisphosphane dppf™ [J].
Petrov, Alex R. ;
Elfferding, Michael ;
Moebus, Juri ;
Harms, Klaus ;
Rufanov, Konstantin A. ;
Sundermeyer, Joerg .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2010, (26) :4157-4165
[40]   TRIPHENYLPHOSPHONIUMCYCLOPENTADIENYLIDE [J].
RAMIREZ, F ;
LEVY, S .
JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (04) :488-489