An Ethynyl-Substituted 1,5,7-Trimethyl-3-azabicyclo[3.3.1]nonan-2-one as a Versatile Precursor for Chiral Templates and Chiral Photocatalysts

被引：7

作者：

Voss, Felix ^{[1
]}

Bach, Thorsten ^{[1
]}

机构：

[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany

来源：

SYNLETT | 2010年 / 10期

关键词：

cycloadditions; cyclobutanes; enantioselectivity; heterocycles; organocatalysis; photochemistry; ENANTIOSELECTIVE PHOTOCHEMICAL-REACTIONS; REDUCTIVE RADICAL CYCLIZATION; TERMINAL ALKYNES; AZIDES; HOST; PHOTOCYCLOADDITION; CYCLOADDITIONS; CONFIGURATION; DERIVATIVES; INHIBITORS;

D O I：

10.1055/s-0029-1219920

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title compound was synthesized and separated into its enantiomers. The enantiomerically pure alkyne was ligated to several aryl azides and aryl halides. The resulting 7-substituted 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-ones were used either as chiral templates in the intramolecular [2+2] photocycloaddition of 4-allyloxyquinolone (up to 72% ee) or as a chiral photocatalyst for the intramolecular [2+2] photocycloaddition of 4-(3-butenyloxy)quinolone (up to 79% ee with 10 mol% catalyst).

引用

页码：1493 / 1496

页数：4

共 21 条

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Bergmann, H
Grosch, B
Sitterberg, S
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JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03): : 970 - 973
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Bach, T
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Grosch, B
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Herdtweck, E
SYNTHESIS-STUTTGART, 2001, (09): : 1395 - 1405
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BUCHANAN, GL
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (15) : 814 - 815
[4] CONFORMATIONAL STUDY OF THE 1-AZABICYCLO[3.3.1]NONAN-2-ONE SYSTEM - MOLECULAR-MECHANICS CALCULATIONS AND X-RAY STRUCTURE OF 5-PHENYL-1-AZABICYCLO[3.3.1]NONAN-2-ONE
BUCHANAN, GL
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SIM, GA
WHITE, DNJ
COX, PJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (11): : 1709 - 1712
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (11): : 2669 - 2670
[6] Synthesis of 1,5,9-trimethyl-6-thia-2-azabicyclo[3.2.2]nonan-3-one by the Ritter reaction
L. A. Baeva
A. A. Fatykhov
E. G. Galkin
N. K. Lyapina
Russian Journal of Organic Chemistry, 2014, 50 : 1851 - 1852
[7] Synthesis of 1,5,9-trimethyl-6-thia-2-azabicyclo[3.2.2]nonan-3-one by the Ritter reaction
Baeva, L. A.
Fatykhov, A. A.
Galkin, E. G.
Lyapina, N. K.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (12) : 1851 - 1852
[8] ANTI-BREDT MOLECULES .3. 3-OXA-1-AZABICYCLO[3.3.1]NONAN-2-ONE AND 6-OXA-1-AZABICYCLO[3.2.1]OCTAN-7-ONE, 2 ATOM-BRIDGED BICYCLIC URETHANES POSSESSING BRIDGEHEAD NITROGEN
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ELSHEKEIL, A
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (26): : 5325 - 5328
[9] Toward the development of a general chiral auxiliary.: Part 6:: Structural effects on diastereoselection using camphor derived lactams:: evaluation of (1R,4S)-1,7,7-trimethyl-3-azabicyclo[2.2.1]hept-5-en-3-one as a chiral controller
Boeckman, RK
Laci, MA
Johnson, AT
TETRAHEDRON-ASYMMETRY, 2001, 12 (02) : 205 - 217
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SPECKAMP, WN
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