Straightforward synthesis of α-substituted prolines by cross-metathesis

被引：14

作者：

Lumini, Marco ^{[1
]}

Cordero, Franca M. ^{[1
]}

Pisaneschi, Federica ^{[1
]}

Brandi, Alberto ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, Lab Progettaz Sintesi & Studio Eterocicli Biol At, I-50019 Sesto Fiorentino, FI, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 16期

关键词：

amino acids; nitrogen heterocycles; cross-coupling; metathesis; microwave;

D O I：

10.1002/ejoc.200800044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of several a-substituted N-Boc-protected prolines has been achieved by cross metathesis (CM) of N-Boc-allylproline 5 with terminal long chain alkenes and alkenes bearing hydroxy, silyloxy, ester, and O-acetylglucosamido groups. The CM occurred with good selectivity and short reaction time under microwave heating conditions, affording yields in the range of 40-92 %. Addition of Ti(OiPr)(4) as a Lewis acid allowed a slight increase of the yield in the case of alkenes with Lewis basic substituents. The CM was also successfully applied to allylproline protected with trichloroacetaldehyde 4, but the intermediate products were less practical for further deprotection and elaboration. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：2817 / 2824

页数：8

共 50 条

[1] Straightforward Access to α-Methylamines through Cross-Metathesis
Poulhes, Florent
Sylvain, Remy
Perfetti, Patricia
Bertrand, Michele P.
Gil, Gerard
Gastaldi, Stephane
SYNTHESIS-STUTTGART, 2010, (08): : 1334 - 1338
[2] Merging Cross-Metathesis and Radical Cyclization: A Straightforward Access to 4-Substituted Benzosultams
Feuillastre, Sophie
Pelotier, Beatrice
Piva, Olivier
SYNTHESIS-STUTTGART, 2013, 45 (06): : 810 - 816
[3] Substituted Pyrroles via Olefin Cross-Metathesis
Donohoe, Timothy J.
Race, Nicholas J.
Bower, John F.
Callens, Cedric K. A.
ORGANIC LETTERS, 2010, 12 (18) : 4094 - 4097
[4] Straightforward synthesis of α,β-unsaturated thioesters via ruthenium-catalyzed olefin cross-metathesis with thioacrylate
van Zijl, Anthoni W.
Minnaard, Adriaan J.
Feringa, Ben L.
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5651 - 5653
[5] Synthesis of dipeptide isosteres by cross-metathesis
Enholm, J. Eric
Low, Tammy
Cooper, Daniel
Ghivirija, Ion
TETRAHEDRON, 2012, 68 (34) : 6920 - 6927
[6] Synthesis of vinyl-functionalized thiazoles by cross-metathesis and tandem Stille coupling/cross-metathesis
Dash, Jyotirmayee
Arseniyadis, Stellios
Cossy, Janine
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (1-2) : 152 - 156
[7] Cross-metathesis in the synthesis of bioactive phosphonates
Agrofoglio, Luigi A.
Kumamoto, Hiroki
Roy, Vincent
CHIMICA OGGI-CHEMISTRY TODAY, 2006, 24 (06) : 16 - 18
[8] Synthesis of glycoporphyrins by cross-metathesis reactions
da Silva, Fernando de C.
Ferreira, Vitor F.
de Souza, Maria C. B. V.
Tome, Augusto C.
Neves, Maria G. P. M. S.
Silva, Artur M. S.
Cavaleiro, Jose A. S.
SYNLETT, 2008, (08) : 1205 - 1207
[9] Synthesis of substituted P-stereogenic vinylphosphine oxides by olefin cross-metathesis
Demchuk, OM
Pietrusiewicz, KM
Michrowska, A
Grela, K
ORGANIC LETTERS, 2003, 5 (18) : 3217 - 3220
[10] Carbonyl-Substituted Nickelocenes by the Cross-Metathesis Route
Buchowicz, Wlodzimierz
Szmajda, Magdalena
ORGANOMETALLICS, 2009, 28 (23) : 6838 - 6840

← 1 2 3 4 5 →