Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine-Catalyzed [3+2]?Annulations

被引：42

作者：

Duvvuru, Deepti ^{[1
]}

Pinto, Nathalie ^{[1
]}

Gomez, Catherine ^{[1
]}

Betzer, Jean-Francois ^{[1
]}

Retailleau, Pascal ^{[1
]}

Voituriez, Arnaud ^{[1
]}

Marinetti, Angela ^{[1
]}

机构：

[1] Ctr Rech Gif, CNRS, UPR 2301, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 2-3期

关键词：

3+2]?cyclization; enantioselective organocatalysis; phosphines; spiro compounds; sulfoxides; ASYMMETRIC 3+2 CYCLOADDITION; ELECTRON-DEFICIENT OLEFINS; FUNCTIONALIZED CYCLOPENTENES; ANTIMYCOBACTERIAL EVALUATION; 1,3-DIPOLAR CYCLOADDITION; CONTAINING LIGANDS; GLUTAMATE ANALOGS; CYCLIZATIONS; SULFOXIDES; EFFICIENT;

D O I：

10.1002/adsc.201100748

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of highly functionalized heterocyclic spiranes has been carried out by [3+2] cyclizations between allenoates and enones, under phosphine catalysis. Excellent enantioselectivity levels (ees up to 99%) have been attained in FerroPHANE-promoted cyclizations of this class, leading to chiral sulfides with unprecedented spiranic structures. The corresponding sulfoxides have been obtained then via a subsequent, highly diastereoselective oxidation of the prostereogenic sulfur centre.

引用

页码：408 / 414

页数：7

共 50 条

[41] Synthesis of carbocyclic hydantocidins via regioselective and diastereoselective phosphine-catalyzed [3+2]-cycloadditions to 5-methylenehydantoins
Pham, TQ
Pyne, SG
Skelton, BW
Whitet, AH
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16): : 6369 - 6377
[42] Asymmetric Construction of Spirocyclopentenebenzofuranone Core Structures via Highly Selective Phosphine-Catalyzed [3+2] Cycloaddition Reactions
Albertshofer, Klaus
Tan, Bin
Barbas, Carlos F., III
ORGANIC LETTERS, 2013, 15 (12) : 2958 - 2961
[43] Phosphine-Catalyzed Sequential [3+2]/[3+2] Annulation between Allenoates and Arylidenemalononitriles for the Enantioselective Construction of Bicyclo[3,3,0]octenes and Cyclopenta[c]quinolinones
Wang, Nengzhong
Lang, Yimin
Wang, Junjie
Wu, Zugen
Lu, Yixin
ORGANIC LETTERS, 2022, 24 (20) : 3712 - 3716
[44] Phosphine-Catalyzed Stereospecific and Enantioselective Desymmetrizative [3+2] Cycloaddition of MBH Carbonates and N-(2-tert-Butylphenyl)maleimides
Hou, Jie
Hao, Wei
Chen, Ying
Wang, Zhen
Yao, Weijun
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 9068 - 9077
[45] An unexpected phosphine-catalyzed [3+2] annulation. Synthesis of highly functionalized cyclopentenes
Lu, Zheng
Zheng, Suqing
Zhang, Xumu
Lu, Xiyan
ORGANIC LETTERS, 2008, 10 (15) : 3267 - 3270
[46] Toward a Predictive Understanding of Phosphine-Catalyzed [3+2] Annulation of Allenoates with Acrylate or Imine
Yu, Zhaoyuan
Jin, Zhichao
Duan, Meng
Bai, Ruopeng
Lu, Yixin
Lan, Yu
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 9729 - 9740
[47] A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol
Du, YS
Lu, XY
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16): : 6463 - 6465
[48] Phosphine-Catalyzed Atroposelective Formal [3+2] Cycloaddition Desymmetrization of N-Arylmaleimides
Wang, Huamin
Wei, Yibo
Li, Yuqiang
Long, Shuangshuang
Sun, Li-Juan
Li, Shixiong
Lin, Ying-Wu
ORGANIC LETTERS, 2022, 24 (36) : 6494 - 6498
[49] Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3+2] annulation of the Morita-Baylis-Hillman carbonates with pyrazoloneyldiene oxindoles
Zhang, Jing
Chan, Wai-Lun
Chen, Ligong
Ullah, Nisar
Lu, Yixin
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2210 - 2214
[50] Phosphine-Catalyzed [3+2] and [2+4] Annulations of γ-Methyl Allenoates with Aryl α-Keto Esters: Stereoselective Syntheses of Functionalized Tetrahydrofurans and 4-Chromanols
Qin, Zifeng
Liu, Rongfang
Zhou, Rong
Li, Ruifeng
He, Zhengjie
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (01) : 86 - 93

← 1 2 3 4 5 →