Lewis acid mediated diastereoselective keto-ene cyclization on chiral perhydro-1,3-benzoxazines: synthesis of enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines

被引:18
作者
Andres, Celia [1 ]
Gonzalez, Israel
Nieto, Javier
Roson, Carlos D.
机构
[1] Univ Valladolid, CINQUIMA, E-47011 Valladolid, Spain
关键词
Carbonyl-ene cyclization; Chiral; 3-hydroxypyrrolidines; Perhydro-1,3-benzoxazines; Diastereoselective synthesis; Lewis acids; INTRAMOLECULAR CARBONYL ENE; IMDA REACTION; DERIVATIVES; OXIDATION; CATALYSTS; ALCOHOLS; ETHERS; ENTRY;
D O I
10.1016/j.tet.2009.09.091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral 2-acyl-3-allyl-perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol were easily cyclized in the presence of Lewis acids at 0 degrees C. The diastereoselectivity of the cyclization was dependent on the nature of the Lewis acid. The cyclization compounds can be transformed into enantiopure cis-3,4-disubstituted 3-hydroxypyrrolidines by ring opening of the N,O-acetal moiety and subsequent elimination of the menthol appendage. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9728 / 9736
页数:9
相关论文
共 36 条
[1]   Synthesis of enantiopure highly substituted trans-8a-hydroxydecahydroisoquinolines by sequential diastereoselective IMDA reaction and oxanorbornene nucleophilic ring opening [J].
Andrés, C ;
Nieto, J ;
Pedrosa, R ;
Vicente, M .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8570-8573
[2]   Asymmetric synthesis of 1-Boc-3- and 4-hydroxypyrrolidines [J].
Aoyagi, Y ;
Williams, RM .
TETRAHEDRON, 1998, 54 (43) :13045-13058
[4]  
Cheung CM, 2001, SYNLETT, P1611
[5]   The carbonyl ene reaction [J].
Clarke, Matthew L. ;
France, Marcia B. .
TETRAHEDRON, 2008, 64 (38) :9003-9031
[7]   NITROALKENE [4+2]-CYCLOADDITIONS WITH 2-(ACYLOXY)VINYL ETHERS - STEREOSELECTIVE SYNTHESIS OF 3-HYDROXY-4-SUBSTITUTED-PYRROLIDINES [J].
DENMARK, SE ;
SCHNUTE, ME .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4576-4595
[8]   Ligands derived from C-aryl substituted derivatives of cyclen: formation of kinetically unstable complexes with lanthanide(III) ions [J].
Edlin, CD ;
Faulkner, S ;
Parker, D ;
Wilkinson, MP ;
Woods, M ;
Lin, J ;
Lasri, E ;
Neth, F ;
Port, M .
NEW JOURNAL OF CHEMISTRY, 1998, 22 (12) :1359-1364
[9]   HIGHLY STEREOSELECTIVE SYNTHESES INVOLVING N-ALKYL-4,4,7-ALPHA-TRIMETHYL-TRANS-OCTAHYDRO-1,3-BENZOXAZINE INTERMEDIATES .2. [J].
ELIEL, EL ;
HE, XC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2114-2119
[10]   The oxidation of metanitrobenzoylformaldehyde. [J].
Evans, WL ;
Witzemann, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1911, 33 :1772-1779