Abstract
The addition of functionalized organolithium compounds derived from 5-chloro-2-methoxy-1-pentene and 6-chloro-2-methoxy-1-hexene to N-tert-butanesulfinyl aldimines imines, and a subsequent hydrolysis of the enol ether moiety, yielded different δ- and ε-amino ketone derivatives, respectively, in moderate yields and diastereoselectivities. The application of these compounds in organic synthesis was demonstrated by the preparation of 2-substituted 6-methylpiperidines in a stereoselective manner, among them natural alkaloids (+)- and (−)-isosolenopsin A.
Highlights
Amino carbonyl compounds are versatile intermediates in organic synthesis to access complex nitrogen-containing molecules
Those derived from tert-butanesulfinamide are of special relevance and have been recurrently used in organic synthesis [14,15,16]
Our research group have accomplished the stereoselective synthesis of α-amino ketone derivatives in moderate yields from β-nitro amine derivatives that were obtained by a coupling reaction of N-tertbutanesulfinyl imines and nitroethane under basic conditions [17] (Scheme 1)
Summary
Amino carbonyl compounds are versatile intermediates in organic synthesis to access complex nitrogen-containing molecules. Some amino carbonyl compounds display biological activity by themselves and have multiple applications in medicinal chemistry For these reasons, the development of methodologies to prepare amino carbonyl compounds is a topic of great interest in organic synthesis [1]. The preparation of α- [2] and β-amino [3,4,5,6,7,8,9,10,11,12,13] ketones have been extensively studied, and in many of the methodologies leading to these compounds, nucleophilic additions to chiral imines are involved Among chiral imines, those derived from tert-butanesulfinamide are of special relevance and have been recurrently used in organic synthesis [14,15,16]. SSyynntthheessiiss ooff αα-- aanndd ββ--aammiinnoo kkeettoonnee ddeerriivvaattiivveess ffrroomm NN--tteerrtt--bbuuttaannoossuullfiffiinnyyll iiimmmiiinnneesss. T7ch’i)s. mTheitshomdeotlhoogdyoallologwy eadlloawcceedss atcocethssetcootrhreescpoornredsipnognednianngtieonmanertisoemnte-r7saenndt-7enatn-7d eonftt-h7’eosef tNh-etseertN-b-utetratn-beusutalfinnesyul lδf-inamyliδn-o akmeitnoonekdeteorniveadtievreisvabtyivuessinbgyausssintagrtainsgstmarattienrgiamlsa(tSeSr)i-aNls-t(eSrSt)--bNu-ttaenrte-sbuultfiannyelsiumlfiinneysl einmt-in5,east enittw-5a, satexitemwapslifiexeedmfoprliifmieidnefsorenimt-5ianeasnednetn-5ta-5aenddereinvte-d5efrdoemrivbeednzfarlodmehbyednezaanlddedhoyddeecaanndal, droedspeceacntiavle, lrye.spAesctaivliemlyi.taAtsioanl,imhaitloatgieonn,ahtaolmogs,enesatteor,mnsi,treislteera,nnditcrialrebaonndylcagrrboounpysl wgriollunpost wbielltnooletrbaetetdoleinratthedesienttrhaenssefotrramnasftoiornmsa, tdiounest,odutheetoexthtreeemxetrlyemreedlyurcetidvuecrtievaectrieoanctmioendmiuemd(iFuimgu(rFei1g)u.re 1)
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