1985
DOI: 10.1021/jo00217a017
|View full text |Cite
|
Sign up to set email alerts
|

Stereospecific syntheses of the four diastereomeric 2-amino-5-phenoxycyclopentanols

Abstract: Stereospecific synthetic routes are described for the formation of the three contiguous chiral centers in the four diastereomeric 2-aminc-5-phenoxycyclopentanols la-4a. All four stereoisomers (la-4a) were prepared, starting from 3-chlorocyclopentene (6). Among the key steps in the syntheses was the development of a mild method for the formation of the aromatic ether linkage in cis-2-phenoxy-6-oxabicyclo[3.l.0]hexane (9) while maintaining the stereochemistry at the three adjacent centers on the cyclopentane rin… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

0
13
0

Year Published

1986
1986
2018
2018

Publication Types

Select...
8
2

Relationship

0
10

Authors

Journals

citations
Cited by 19 publications
(13 citation statements)
references
References 0 publications
0
13
0
Order By: Relevance
“…It was established experimentally that cesium carbonate can be used as a catalyst for the ring-oprning reactions of 3-substituted carbocyclic epoxides instead of sodium hydride, the common reagent for the epoxide cleavage with phenols. [17][18][19] Cesium carbonate is easier to handle, and it is not necessarily to generate a phenolate before adding an epoxide to the reaction mixture. Additionally, this method allows to avoid overloading of the reagents in comparison with the reactions employing sodium hydride.…”
Section: Resultsmentioning
confidence: 99%
“…It was established experimentally that cesium carbonate can be used as a catalyst for the ring-oprning reactions of 3-substituted carbocyclic epoxides instead of sodium hydride, the common reagent for the epoxide cleavage with phenols. [17][18][19] Cesium carbonate is easier to handle, and it is not necessarily to generate a phenolate before adding an epoxide to the reaction mixture. Additionally, this method allows to avoid overloading of the reagents in comparison with the reactions employing sodium hydride.…”
Section: Resultsmentioning
confidence: 99%
“…Using sodium azide, cyclopentene oxide was opened in ammonium chloride and aqueous ethanol. 18 The azide was reduced using triphenyl phosphine and gradual heating in toluene; rapid heating caused effervescence and the release of N 2 gas. The resulting amine was protected in situ in a biphasic mixture of di-tert-butyl dicarbonate, ethyl acetate and a saturated aqueous solution of sodium bicarbonate, to afford 15 in 22% yield over three steps.…”
Section: Precursor Synthesismentioning
confidence: 99%
“…Synthesis of 8 and 9 was accomplished in 8 stages from the azido alcohol 10, which was obtained from cyclopentene oxide by ring opening with sodium azide (Scheme 1). 13 Triphenylphosphine reduction of 10 and treatment with di-tert-butyl dicarbonate afforded the protected aminol 11 (41% yield) as a crystalline solid. Under Mitsunobu conditions 11 was cleanly converted to the Boc protected aziridine 12 in high yield (79%).…”
Section: Synthesis Of the Lactams 4 Andmentioning
confidence: 99%