CYCLOBUTYL PHENYL SULFOXIDE AND (SR)-CYCLOBUTYL P-TOLYL SULFOXIDE - NEW REAGENTS FOR THE SPIROANNELATION OF CYCLOPENTANONE

被引：9

作者：

FITJER, L ^{[1
]}

SCHLOTMANN, W ^{[1
]}

NOLTEMEYER, M ^{[1
]}

机构：

[1] UNIV GOTTINGEN,INST ANORGAN CHEM,D-37077 GOTTINGEN,GERMANY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 28期

关键词：

D O I：

10.1016/00404-0399(50)0958F-

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclohutyl phenyl sulfide 2, cyctobutyl phenyl sulfoxide 3 and (SR)-cyclobutyl p-tolyl sulfoxide (SR)-8 have been synthesized and used for the spiroannelation cyclopentanone. In the most effective sequence, lithiated 3 is added to ketones with formation of beta-hydroxy sulfoxides 4a-g, which are ring enlarged and hydrolyzed to cyclopentanones 6a-e and sulfanylcyclopentene 6f, respectively, after reduction to beta-hydroxy sulfides 5a-f. In an asymmetric version using (SR)-8, partial racemization during ring enlargement was observed.

引用

页码：4985 / 4988

页数：4

共 20 条

[1] CONFIGURATIONAL RELATIONSHIPS AMONG SOME SULFOXIDES
ANDERSEN, KK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) : 1953 - &
[2] THE PREPARATION OF CYCLOBUTANE
CASON, J
WAY, RL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1949, 14 (01) : 31 - 36
[3] PHENYLTHIOMETHYLLITHIUM AND BIS(PHENYLTHIO)METHYLLITHIUM
COREY, EJ
SEEBACH, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) : 4097 - &
[4] DRABOWICZ J, 1978, SYNTHESIS-STUTTGART, P139
[5] FUJITA T, 1986, CHEM IND-LONDON, P427
[6] 1,2-ASYMMETRIC REARRANGEMENTS IN CHIRAL SULFINYLCYCLOPROPANE SYSTEMS - ASYMMETRIC-SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED CYCLOBUTANONES
HIROI, K
NAKAMURA, H
ANZAI, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1249 - 1250
[7] STEREOCHEMISTRY OF ASYMMETRIC 1,2-REARRANGEMENTS OF CHIRAL SULFENYL-CYCLOPROPANES INTO CYCLOBUTANE DERIVATIVES - A NOVEL ENTRY TO CHIRAL CYCLOBUTANE SYSTEMS USING CHIRAL SULFINYL GROUPS
HIROI, K
OGATA, T
[J]. CHEMISTRY LETTERS, 1990, (04) : 527 - 530
[8] STEREOSELECTIVE SYNTHESIS AND STEREOSPECIFIC ASYMMETRIC 1,2-REARRANGEMENTS OF CHIRAL SULFINYLCYCLOPROPANE DERIVATIVES
HIROI, K
ANZAI, T
OGATA, T
SAITO, M
[J]. TETRAHEDRON LETTERS, 1990, 31 (02) : 239 - 242
[9] NUCLEOPHILIC ALKYLIDENE TRANSFER REAGENTS - ETHYLIDES, ISOPROPYLIDES, AND CYCLOPROPYLIDES DERIVED FROM SALTS OF SULFOXIMINES
JOHNSON, CR
JANIGA, ER
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) : 7692 - 7700
[10] PREPARATION AND REACTIONS OF SOME ALKYLTHIOMETHYLLITHIUM COMPOUNDS
PETERSON, DJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (06) : 1717 - &

← 1 2 →