Mercury(II) chloride-mediated cyclization -: Rearrangement of O-propargylglycolaldehyde dithioacetals to 3-pyranone dithioketals:: An expeditious access to 3-pyranones

被引：8

作者：

Ghorai, S ^{[1
]}

Bhattacharjya, A ^{[1
]}

机构：

[1] Indian Inst Chem Biol, Kolkata 700032, W Bengal, India

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 02期

关键词：

D O I：

10.1021/ol047893a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

O-Propargyl glycolaldehyde dithioacetals undergo a unique cyclization-rearrangement in the presence of mercuric chloride and calcium carbonate to afford 3-pyranones exclusively or along with 2,5-dihydrofuran-3-carboxaldehydes via their dithioketals and dithioacetals.

引用

页码：207 / 210

页数：4

共 22 条

[1]

BALASUBR.KK, 1973, TETRAHEDRON LETT, P5003

[2] ACID CATALYSIS OF CLAISEN REARRANGEMENT .1. FORMATION OF 4,4'-BIS (2H-CHROMENYL)MERCURY DERIVATIVES FROM ARYL 2-PROPYNYL ETHERS [J].

BATES, DK ;

JONES, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) :3775-3776

[3] ENANTIOMERICALLY PURE BUILDING-BLOCKS FROM SUGARS .11. DIELS-ALDER REACTIONS OF PYRANOID ENOLONE ESTERS WITH CYCLOPENTADIENE UNDER THERMAL, LEWIS ACID CATALYSIS, AND HIGH-PRESSURE CONDITIONS [J].

DAUBEN, WG ;

KOWALCZYK, BA ;

LICHTENTHALER, FW .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2391-2398

[4] ALDEHYDES AND KETONES FROM THIOACETALS [J].

FETIZON, M ;

JURION, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (07) :382-&

[5] Electrophile mediated heteroatom cyclizations onto C-C pi-bonds .2. Metal ion mediated cyclization [J].

Frederickson, M ;

Grigg, R .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1997, 29 (01) :63-115

[6]

Green T. F., 1999, PROTECTIVE GROUPS OR, p[329, 724]

[7]

HEPWORTH JD, 1984, COMPREHENSIVE HETERO, V3, P843

[8] Mercuric triflate-catalyzed synthesis of 2-methylfurans from 1-alkyn-5-ones [J].

Imagawa, H ;

Kurisaki, T ;

Nishizawa, M .

ORGANIC LETTERS, 2004, 6 (21) :3679-3681

[9] Synthetic approach to analogues of the original structure of sclerophytin A [J].

Jung, ME ;

Pontillo, J .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (19) :6848-6851

[10] Asymmetric oxidopyrylium-alkene[5+2] cycloaddition: a divergent approach for the synthesis of enantiopure oxabicyclo[5.4.0]undecanes [J].

Krishna, UM ;

Deodhar, KD ;

Trivedi, GK .

TETRAHEDRON, 2004, 60 (22) :4829-4836

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