Stereoselective synthesis of 5-7 membered cyclic ethers by deiodonative ring-enlargement using hypervalent iodine reagents

被引：16

作者：

Abo, T ^{[1
]}

Sawaguchi, M ^{[1
]}

Senboku, H ^{[1
]}

Hara, S ^{[1
]}

机构：

[1] Hokkaido Univ, Div Mol Chem, Grad Sch Engn, Sapporo, Hokkaido 0608628, Japan

来源：

MOLECULES | 2005年 / 10卷 / 01期

关键词：

ring-enlargement; cyclic ether; hypervalent iodine compounds;

D O I：

10.3390/10010183

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Stereoselective synthesis of 5-7 membered cyclic ethers was achieved by deiodonative ring-enlargement of cyclic ethers having an iodoalkyl substituent. The reaction took place readily under mild conditions using hypervalent iodine compounds and an acetoxy or a trifluoroacetoxy group was introduced into the rings depending on the hypervalent iodine reagent employed. The use of hexafluoroisopropanol (HFIP) as solvent is critical.

引用

页码：183 / 189

页数：7

共 17 条

[1] A SIMPLE AND VERY STEREOSELECTIVE SYNTHESIS OF D,L-MUSCARINE
AMOUROUX, R
GERIN, B
CHASTRETTE, M
[J]. TETRAHEDRON LETTERS, 1982, 23 (42) : 4341 - 4344
[2] Preparation of oxepanes, oxepenes, and oxocanes by iodoetherification using bis(sym-collidine)iodine(I) hexafluorophosphate as electrophile
Brunel, Y
Rousseau, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) : 5793 - 5800
[3] Chemoenzymatic synthesis of the enantiomers of desoxymuscarine
Conti, P
Dallanoce, C
De Amici, M
De Micheli, C
Carrea, G
Zambianchi, F
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (04) : 657 - 665
[4] The iodocyclization of unsaturated dihydroxysulfonamide derivatives.: N- versus O-cyclization
Cossy, J
Tresnard, L
Belotti, D
Pardo, DG
[J]. TETRAHEDRON LETTERS, 2001, 42 (02) : 251 - 254
[5] EVANS RD, 1988, SYNTHESIS-STUTTGART, P862
[6] Efficient synthesis of 2,3-trans-tetrahydropyrans and oxepanes:: Rearrangement-ring expansion of cyclic ethers having a chloromethanesulfonate
Hori, N
Nagasawa, K
Shimizu, T
Nakata, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (11) : 2145 - 2148
[7] FLUORINE-DIRECTED NAZAROV CYCLIZATIONS - A CONTROLLED SYNTHESIS OF CROSS-CONJUGATED 2-CYCLOPENTEN-1-ONES
ICHIKAWA, J
MIYAZAKI, S
FUJIWARA, M
MINAMI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) : 2320 - 2321
[8] Fluorinative ring-expansion of cyclic ethers using p-iodotoluene difluoride.: Stereoselective synthesis of fluoro cyclic ethers
Inagaki, T
Nakamura, Y
Sawaguchi, M
Yoneda, N
Ayuba, S
Hara, S
[J]. TETRAHEDRON LETTERS, 2003, 44 (21) : 4117 - 4119
[9] Synthesis of methylene-expanded 2′,3′-dideoxyribonucleosides
Jung, ME
Kiankarimi, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) : 8133 - 8144
[10] Stereocontrol of 5-endo-trig cyclisations by hydroxyl groups:: a formal short synthesis of (+)-muscarine
Knight, DW
Staples, ER
[J]. TETRAHEDRON LETTERS, 2002, 43 (38) : 6771 - 6773

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