Novel route to functionalized cyclooctanoids via [5+3] cycloaddition

被引：13

作者：

Krishna, UM ^{[1
]}

Deodhar, KD ^{[1
]}

Trivedi, GK ^{[1
]}

Mobin, SM ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Natl Single Crystal Xray Diffract Facil, Bombay 400076, Maharashtra, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 03期

关键词：

D O I：

10.1021/jo0353583

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The self-dimerization of 3-oxidopyrylium leading to stereocontrolled formation of highly functionalized cyclo-octanoids is described. Different functionalities were introduced on the dimer (3) and the stereochemical outcome was determined by single-crystal X-ray analysis. It is noteworthy that the hydrogenation of 3 in ethanol solvent gave the transannulated product 5, whereas the expected dihydro product 4 was obtained when the reaction was run in nonnucleophilic solvents. The mechanistic pathway is discussed.

引用

页码：967 / 969

页数：3

共 50 条

[1] [5+3] Cycloaddition of 3-Oxidopyrylium: A Novel Route to Functionalized Cyclooctanoids from Furans
Krishna, Urlam Murali
Patil, Mahendra P.
Sunoj, Raghavan B.
Trivedi, Girish K.
[J]. SYNTHESIS-STUTTGART, 2010, (02): : 320 - 328
[2] Synthesis of Chiral Diazocine Derivatives via a Copper-Catalyzed Dearomative [5+3] Cycloaddition
Lee, Ju Young
Varshnaya, Rohit Kumar
Yoo, Eun Jeong
[J]. ORGANIC LETTERS, 2022, 24 (20) : 3731 - 3735
[3] Thermal [5+3] cycloaddition reaction: Total synthesis of jujuyane.
Lee, HY
Kim, BG
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U54 - U54
[4] [6+3] cycloaddition of pentafulvenes with 3-oxidopyrylium betaine: a novel methodology toward the synthesis of 5-8 fused oxabridged cyclooctanoids
Krishnan, K. Syam
Sajisha, V. S.
Anas, S.
Suresh, C. H.
Bhadbhade, Mohan M.
Bhosekar, Gaurav V.
Radhakrishnan, K. V.
[J]. TETRAHEDRON, 2006, 62 (25) : 5952 - 5961
[5] Novel route to functionalized tetraaryltetra[2,3]naphthaloporphyrins via oxidative aromatization
Finikova, OS
Cheprakov, AV
Carroll, PJ
Vinogradov, SA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19): : 7517 - 7520
[6] Functionalized organosilica microspheres via a novel emulsion-based route
Miller, CR
Vogel, R
Surawski, PPT
Jack, KS
Corrie, SR
Trau, M
[J]. LANGMUIR, 2005, 21 (21) : 9733 - 9740
[7] Enantiocontrolled synthesis of highly functionalized tropanes via [5+2] cycloaddition to η3-pyridinylmolybdenum π-complexes
Malinakova, HC
Liebeskind, LS
[J]. ORGANIC LETTERS, 2000, 2 (24) : 3909 - 3911
[8] “5+3”创意学习模式
汤钦飞
樊功厚
林娅妮
[J]. 北京支部生活, 2010, (09) : 13 - 14
[9] NOVEL AND FACILE ROUTE TO (+/-)-PHYSOVENINE VIA INTRAMOLECULAR [2+2]CYCLOADDITION REACTION
SHISHIDO, K
AZUMA, T
SHIBUYA, M
[J]. TETRAHEDRON LETTERS, 1990, 31 (02) : 219 - 220
[10] 冬日护肤提醒5+3
邢嬛
[J]. 父母必读, 2012, (11) : 32 - 33

← 1 2 3 4 5 →