Asymmetric amine-intercepted nazarov cyclization

被引：68

作者：

Dhoro, Francis

Kristensen, Tor E.

Stockmann, Vegar

Yap, Glenn P. A.

Tius, Marcus A.

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

[2] Univ Delaware, Newark, DE 19716 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 23期

关键词：

D O I：

10.1021/ja0718873

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The chiral auxiliary directed addition of a propargyllithium reagent to a morpholino enamide, followed by exposure of the adduct to activated dry Florisil in the absence of solvent and in the presence of a primary or secondary amine, leads to a cascade of reactions that results in the formation of an aminocyclopentenone as a single diastereoisomer. The reaction can also be conducted intramolecularly.

引用

页码：7256 / +

页数：3

共 19 条

[11] MARIELLA PR, 1961, J ORG CHEM, V26, P3217
[12] Recent developments in the Nazarov process
Pellissier, H
[J]. TETRAHEDRON, 2005, 61 (27) : 6479 - 6517
[13] Intramolecular azide trapping of the nazarov intermediate: Formation of peroxy-bridged indolizidinones via a deep-seated rearrangement and aerobic oxidation
Rostami, Ali
Wang, Yong
Arif, Atta M.
McDonald, Robert
West, F. G.
[J]. ORGANIC LETTERS, 2007, 9 (04) : 703 - 706
[14] Some new Nazarov chemistry
Tius, MA
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (11) : 2193 - 2206
[15] Cationic cyclopentannelation of allene ethers
Tius, MA
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 284 - 290
[16] Cross-conjugated cyclopentenone prostaglandins synthesis of Δ7-10-chloro-15-deoxy PGA1 ethyl ester
Tius, MA
Busch-Petersen, J
Yamashita, M
[J]. TETRAHEDRON LETTERS, 1998, 39 (24) : 4219 - 4222
[17] Cyclizations of α-diketones to α-hydroxycyclopentenones on silica gel in the absence of solvent
Uhrich, Elizabeth A.
Batson, William A.
Tius, Marcus A.
[J]. SYNTHESIS-STUTTGART, 2006, (13): : 2139 - 2142
[18] Halide trapping of the Nazarov intermediate in strained polycyclic systems: a new interrupted Nazarov reaction
White, TD
West, FG
[J]. TETRAHEDRON LETTERS, 2005, 46 (34) : 5629 - 5632
[19] Convenient route to centro-substituted triquinacene skeletons via the interrupted Nazarov reaction
Yungai, A
West, FG
[J]. TETRAHEDRON LETTERS, 2004, 45 (28) : 5445 - 5448

← 1 2 →