Alkylation of l- and d-menthyl pentanoate with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane

Date

1996-01-01

Author

Demir, Ayhan Sıtkı

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

173
views

0
downloads

The alkylation of l- and d-menthyl valerate with n-hexyl iodide and with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane gave modest levels of diastereoselection. The chirality of the ester group favoured slight degree of selectivity. The chiral centers had limited impact on diastereoselectivity.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/56772

Journal

SYNTHETIC COMMUNICATIONS

DOI

https://doi.org/10.1080/00397919608004775

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Transition structures, energetics, and nucleus-independent chemical shifts for 6 pi electrocyclizations of dienylketenes to cyclohexadienones: A DFT study Zora, Metin (American Chemical Society (ACS), 2004-03-19) 6pi electrocyclizations of dienylketenes to 2,4-cyclohexadienones have been investigated at the (U)B3LYP/6-31G* level and found to be a favored and exothermic process for most dienylketenes. As evidenced by calculations, dienylketene cyclizations proceed via a pseudopericyclic process. If the terminal double bond of dienylketenes is embedded into a benzenoid-type aryl moiety, the partial or complete loss of aromaticity, as indicated by NICS values, increases the activation barrier and makes the reaction les...
ASYMMETRIC ENE REACTIONS OF 2-METHYLPROPENE WITH CHLOROALDEHYDES IN THE PRESENCE OF BORONTRIFLUORIDE-L-MENTHYLETHYL ETHERATE AKHMEDOV, IM; Tanyeli, Cihangir; AKHMEDOV, MA; MOHAMMADI, M; DEMIR, AS (Informa UK Limited, 1994-01-01) The asymmetric ene reactions of prochiral chloroaldehydes, chloral and 2,3-dichlorobutanal with 2-methylpropanal in the presence of BF3 l-menthylethyl etherate gave optically active homoallylic alcohols in 16-22% ee. The dechlorination of the chloro alcohols lead to the unsaturated derivatives of alcohols.
Chemoenzymatic synthesis of enantiomerically enriched 2-oxobicyclo[m.1.0]alkan-3-yl acetate derivatives Atlı, Selin; Tanyeli, Cihangir; Department of Chemistry (2005) a,β-Unsaturated cyclic ketones were selectively oxidized on a'- positions using Mn(OAc)3 and Pb(OAc)4, respectively. The resultant racemic a'-acetoxylated substrates were resolved into corresponding enantiomerically enriched a'-hydroxylated and a'-acetoxylated compounds via PLE hydrolysis. a'-Hydroxylated compounds are racemized quickly, so they were acetylated with acetyl chloride and pyridine in situ to give the corresponding a'-acetoxylated compounds. Resultant a'-acetoxy a,β-unsaturated cyclic ketones r...
Uncatalyzed addition of TMSCN to acylphosphonates Demir, Ayhan Sıtkı; Reis, Omer; Kayalar, Metin; Eymur, Serkan; Reis, Barbaros (Georg Thieme Verlag KG, 2006-12-01) The cyanosilylations of various alkyl- and arylphosphonates under comparatively mild conditions furnished the trimethyl-silyloxycyanophosphonates in high yield. The addition to ketophosphonate functions works without the influence of a catalyst.
Unusual manganese(III)-mediated oxidative free radical additions of 1,3-dicarbonyl compounds to benzonorbornadiene and 7-heterobenzonorbornadienes: Mechanistic studies Caliskan, Rasit; Ali, Mohamed Fadelalla; Sahin, Ertan; Watson, William H.; Balcı, Metin (American Chemical Society (ACS), 2007-04-27) Benzonorbornadiene and heterobenzonorbornadiene were reacted with dimedone/acetylacetone and Mn(OAc)3 in the presence and absence of Cu(OAc)2. The reaction of benzonorbornadiene with dimedone gave mainly the dihydrofuran addition product, whereas the reaction with acetylacetone produced a rearranged product in addition to the dihydrofuran derivative. On the other hand, oxanorbornadiene gave unusual products such as the cycloproponated compound and a product arising from the incorporation of 2 mol of dimedon...

Citation Formats

A. S. Demir, “Alkylation of l- and d-menthyl pentanoate with (20S)-20-iodomethyl-4 alpha-methyl-5 alpha-pregnane,” SYNTHETIC COMMUNICATIONS, pp. 4519–4530, 1996, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56772.