Stereocontrolled formation of amino acids and N-heterocycles bearing a quaternary chiral carbon

被引：42

作者：

Roy, S ^{[1
]}

Spino, C ^{[1
]}

机构：

[1] Univ Sherbrooke, Dipartimento Chim, Sherbrooke, PQ J1K 2R1, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 05期

关键词：

D O I：

10.1021/ol053061g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereocontrolled formation of tertiary or quaternary chiral carbons bearing nitrogen was achieved using the [3,3]-sigmatropic rearrangement of cyanate to isocyanate as a key element. A short and highly selective sequence of reactions, starting from p-menthane-3-carboxaldehyde, was developed leading to alpha,alpha-dialkylated alpha-amino acids or N-heterocycles, depending on the method of cleavage of the auxiliary.

引用

页码：939 / 942

页数：4

共 50 条

[41] Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams
Douglas C. Behenna
Yiyang Liu
Taiga Yurino
Jimin Kim
David E. White
Scott C. Virgil
Brian M. Stoltz
Nature Chemistry, 2012, 4 (2) : 130 - 133
[42] The synthesis of N-heterocycles via copper/TEMPO catalysed aerobic oxidation of amino alcohols
Flanagan, James C. A.
Dornan, Laura M.
McLaughlin, Mark G.
McCreanor, Niall G.
Cook, Matthew J.
Muldoon, Mark J.
GREEN CHEMISTRY, 2012, 14 (05) : 1281 - 1283
[43] Alkenyl and aryl boronates -: Mild nucleophiles for the stereoselective formation of functionalized N-heterocycles
Batey, RA
MacKay, DB
Santhakumar, V
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) : 5075 - 5076
[44] PSEUDO-BASE FORMATION IN N-HETEROCYCLES COORDINATED TO METAL-IONS
GILLARD, RD
HUGHES, CT
WILLIAMS, PA
TRANSITION METAL CHEMISTRY, 1976, 1 (02) : 51 - 52
[45] Cooperative Dehydrogenation of N-Heterocycles Using a Carbon Nanotube-Rhodium Nanohybrid
Jawale, Dhanaji V.
Gravel, Edmond
Shah, Nimesh
Dauvois, Vincent
Li, Haiyan
Namboothiri, Irishi N. N.
Doris, Eric
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (19) : 7039 - 7042
[46] Air oxidized activated carbon catalyst for aerobic oxidative aromatizations of N-heterocycles
Enders, Lukas
Casadio, David S.
Aikonen, Santeri
Lenarda, Anna
Wirtanen, Tom
Hu, Tao
Hietala, Sami
Ribeiro, Lucilia S.
Pereira, Manuel Fernando R.
Helaja, Juho
CATALYSIS SCIENCE & TECHNOLOGY, 2021, 11 (17) : 5962 - 5972
[47] Copper-Catalyzed C-N Bond Formation with N-Heterocycles and Aryl Halides
Boswell, Mikki G.
Yeung, Fanny G.
Wolf, Christian
SYNLETT, 2012, (08) : 1240 - 1244
[48] Asymmetric Allylic Alkylation in Combination with Ring-Closing Metathesis for the Preparation of Chiral N-Heterocycles
Teichert, Johannes F.
Zhang, Suyan
van Zijl, Anthoni W.
Slaa, Jan Willem
Minnaard, Adriaan J.
Feringa, Ben L.
ORGANIC LETTERS, 2010, 12 (20) : 4658 - 4660
[49] Facile tin(ii)-catalyzed synthesis of N-heterocycles from dicarboxylic acids and arylamines
Van Hieu Tran
Kim, Hee-Kwon
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (14) : 2881 - 2888
[50] Aerobic Electrochemical Csp3-N Coupling between Aliphatic Carboxylic Acids and N-heterocycles
Chen, Ruonan
Yuan, Hongyan
Wang, Yawen
Chen, Hongyu
Zhang, Yanhua
ORGANOMETALLICS, 2023, 42 (01) : 1 - 5

← 1 2 3 4 5 →