Asymmetric selenomethoxylation of alkenes with camphorselenenyl sulfate

被引：36

作者：

Tiecco, M ^{[1
]}

Testaferri, L ^{[1
]}

Santi, C ^{[1
]}

Marini, F ^{[1
]}

Bagnoli, L ^{[1
]}

Temperini, A ^{[1
]}

机构：

[1] Univ Perugia, Fac Farm, Ist Chim Organ, I-06100 Perugia, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(98)00252-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By reaction with ammonium persulfate the easily available diselenide derived from (1R)-(+)-camphor was converted into the camphorselenenyl sulfate. This chiral electrophilic selenium reagent reacted at room temperature with alkenes in the presence of methanol to afford selenomethoxylated adducts in good yields and with moderate to good facial selectivity. The two diastereomeric addition products could be separated in most cases. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2809 / 2812

页数：4

共 17 条

[1] 1,3-DISELENETANES AND 1,3-DITHIETANES DERIVED FROM CAMPHOR - FORMATION, STRUCTURE, STEREOCHEMISTRY, AND OXIDATION TO SELENOXIDE AND SULFOXIDE PRODUCTS [J].

BACK, TG ;

DYCK, BP ;

PARVEZ, M .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :703-710

[2]

BACK TG, 1996, J CHEM SOC CHEM COMM, P2567

[3] CHIRAL SYNTHESIS VIA ORGANOBORANES .14. SELECTIVE REDUCTIONS .41. DIISOPINOCAMPHEYLCHLOROBORANE, AN EXCEPTIONALLY EFFICIENT CHIRAL REDUCING AGENT [J].

BROWN, HC ;

CHANDRASEKHARAN, J ;

RAMACHANDRAN, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1539-1546

[4] ELECTROPHILIC SUBSTITUTION AT SATURATED CARBON .3. EFFECT OF SOLVENT COMPOSITION ON REACTION PATH [J].

CRAM, DJ ;

KOPECKY, KR ;

HAUCK, F ;

LANGEMANN, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (21) :5754-5760

[5] 2,6-bis[(2S)-tetrahydrofuran-2-yl]phenyl diselenide: An effective reagent for asymmetric electrophilic addition reactions to olefins [J].

Deziel, R ;

Malenfant, E ;

Thibault, C ;

Frechette, S ;

Gravel, M .

TETRAHEDRON LETTERS, 1997, 38 (27) :4753-4756

[6]

FUJITA K, 1995, TETRAHEDRON LETT, V36, P5219

[7] Design of optically active selenium reagents having a chiral tertiary amino group and their application to asymmetric inter- and intramolecular oxyselenenylations [J].

Fujita, K ;

Murata, K ;

Iwaoka, M ;

Tomoda, S .

TETRAHEDRON, 1997, 53 (06) :2029-2048

[8] ASYMMETRIC INTRAMOLECULAR SELENOETHERIFICATION AND SELENOLACTONIZATION USING AN OPTICALLY-ACTIVE DIARYL DISELENIDE DERIVED FROM D-MANNITOL [J].

FUJITA, KI ;

MURATA, K ;

IWAOKA, M ;

TOMODA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (16) :1641-1642

[9] A HIGHLY SELECTIVE ASYMMETRIC METHOXYSELENYLATION OF ALKENES WITH A CHIRAL FERROCENYLSELENIUM REAGENT [J].

FUKUZAWA, S ;

KASUGAHARA, Y ;

UEMURA, S .

TETRAHEDRON LETTERS, 1994, 35 (50) :9403-9406

[10] Asymmetric methoxyselenenylation of alkenes with chiral ferrocenylselenium reagents [J].

Fukuzawa, S ;

Takahashi, K ;

Kato, H ;

Yamazaki, H .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7711-7716

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