The preparation of a bridgehead organolithium reagent

被引：5

作者：

Harmata, M ^{[1
]}

Kirchhoefer, P ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

SYNLETT | 2003年 / 04期

关键词：

cycloadditions; electrophilic additions; lithium; metalations; metathesis;

D O I：

10.1055/s-2003-37521

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the THP-protected compound 5 with t-BuLi at -78 degreesC in THF/DME affords a new tertiary organolithium species that reacts with a variety of electrophiles in good yield. As an example of the utility of the adducts of such reactions, treatment of 13 with a metathesis catalyst afforded 21 in excellent yield.

引用

收藏

页码：497 / 500

页数：4

相关论文

共 14 条

[1] Suberosenone, a new cytotoxin from Subergorgia suberosa [J].

Bokesch, HR ;

McKee, TC ;

Cardellina, JH ;

Boyd, MR .

TETRAHEDRON LETTERS, 1996, 37 (19) :3259-3262

[2] QUADRONE, A NEW ANTI-TUMOR SUBSTANCE PRODUCED BY ASPERGILLUS-TERREUS PRODUCTION, ISOLATION AND PROPERTIES [J].

CALTON, GJ ;

RANIERI, RL ;

ESPENSHADE, MA .

JOURNAL OF ANTIBIOTICS, 1978, 31 (01) :38-42

[3] A GENERAL METHODOLOGY FOR THE SYNTHESIS OF [2.2.1], [3.2.1+], AND [4.2.1] BRIDGED BICYCLIC DISULFIDE SYSTEMS [J].

FOLKINS, PL ;

HARPP, DN .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2013-2017

[4] Intramolecular 4+3 cycloadditions.: A cyclohexenyl cation, its halogenated congener and a quasi-Favorskii rearrangement [J].

Harmata, M ;

Bohnert, G ;

Kürti, L ;

Barnes, CL .

TETRAHEDRON LETTERS, 2002, 43 (13) :2347-2349

[5] A 4+3 cycloaddition approach to the synthesis of spatol. A formal total synthesis of racemic spatol [J].

Harmata, M ;

Rashatasakhon, P .

ORGANIC LETTERS, 2001, 3 (16) :2533-2535

[6] A 4+3 cycloaddition approach to the spatane ring system [J].

Harmata, M ;

Rashatasakhon, P .

TETRAHEDRON LETTERS, 2001, 42 (33) :5593-5595

[7] 4+3 cycloaddition reactions of halogen-substituted cyclohexenyl oxyallylic cations [J].

Harmata, M ;

Shao, LX ;

Kürti, L ;

Abeywardane, A .

TETRAHEDRON LETTERS, 1999, 40 (06) :1075-1078

[8]

Harmata M, 1999, SYNTHESIS-STUTTGART, P1534

[9] BRIDGEHEAD INTERMEDIATES IN ORGANIC-SYNTHESIS - A REPRODUCIBLE SYNTHESIS OF ADAMANTANE-CONTAINING COMPOUNDS [J].

KRAUS, GA ;

SICLOVAN, TM .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :922-923

[10] HIGH-YIELD DIRECT SYNTHESIS OF A NEW CLASS OF TERTIARY ORGANO-LITHIUM DERIVATIVES OF POLYCYCLIC-HYDROCARBONS [J].

MOLLE, G ;

BAUER, P ;

DUBOIS, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) :2975-2981