Model studies of the overall 5-endo-trig iodocyclization of homoallylic alcohols

被引：45

作者：

Bedford, SB ^{[1
]}

Bell, KE ^{[1
]}

Bennett, F ^{[1
]}

Hayes, CJ ^{[1
]}

Knight, DW ^{[1
]}

Shaw, DE ^{[1
]}

机构：

[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 15期

关键词：

D O I：

10.1039/a902411e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Overall 5-endo-trig iodocyclizations of homoallylic alcohols, with a range of substitution patterns, leading to beta-iodotetrahydrofurans are usually highly efficient and stereoselective when carried out in anhydrous acetonitrile in the presence of sodium hydrogen carbonate. Such cyclizations, which are not exceptions to Baldwin's rules as they are electrophile-driven, appear to proceed via a well-ordered chair-like transition state. The iodine can be replaced by hydroxy, acetoxy and azide groups.

引用

页码：2143 / 2153

页数：11

共 64 条

[1] BORON-TRIFLUORIDE ASSISTED OPENING OF EPOXIDES BY LITHIUM ALKENYL ALUMINATE REAGENTS [J].

ALEXAKIS, A ;

JACHIET, D .

TETRAHEDRON, 1989, 45 (19) :6197-6202

[2] Electrophilic 5-endo-trig cyclisations of 2-silyl-3-alkenols. A stereoselective route to polysubstituted tetrahydrofurans. [J].

Andrey, O ;

Ducry, L ;

Landais, Y ;

Planchenault, D ;

Weber, V .

TETRAHEDRON, 1997, 53 (12) :4339-4352

[3]

[Anonymous], 1992, NMR SPECTROSCOPY

[4] 5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE [J].

BALDWIN, JE ;

CUTTING, J ;

DUPONT, W ;

KRUSE, L ;

SILBERMAN, L ;

THOMAS, RC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :736-738

[5] APPROACH VECTOR ANALYSIS - STEREOCHEMICAL APPROACH TO REACTIVITY [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :738-741

[6] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[7] PREDICTIVE MODELS FOR THE OVERALL 5-ENDO-TRIG IODOCYCLISATION OF HOMOALLYLIC ALCOHOLS [J].

BARKS, JM ;

KNIGHT, DW ;

SEAMAN, CJ ;

WEINGARTEN, GG .

TETRAHEDRON LETTERS, 1994, 35 (39) :7259-7262

[8] A STEREOSELECTIVE APPROACH TO ANNULATED TETRAHYDROFURANS BY IODOCYCLISATIONS OF 2-ALKENYLCYCLOALKAN-1-OLS [J].

BARKS, JM ;

KNIGHT, DW ;

WEINGARTEN, GG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (06) :719-720

[9] ELECTROPHILIC LACTONIZATION AS A TOOL IN ACYCLIC STEREOCONTROL - SYNTHESIS OF SERRICORNIN [J].

BARTLETT, PA ;

RICHARDSON, DP ;

MYERSON, J .

TETRAHEDRON, 1984, 40 (12) :2317-2327

[10] STEREOSELECTIVE EPOXIDATION OF ACYCLIC OLEFINIC CARBOXYLIC-ACIDS VIA IODO-LACTONIZATION [J].

BARTLETT, PA ;

MYERSON, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (12) :3950-3952

← 1 2 3 4 5 6 7 →