Diastereoselectivity in the Addition of Allylzinc Reagents to δ-Alkoxy-γ,δ-disubstituted Alkenyllithium Compounds

Bernard, Nicolas; Chemla, Fabrice; Ferreira, Franck; Mostefai, Naouel; Normant, Jean F.

doi:10.1002/1521-3765(20020715)8:14<3139::aid-chem3139>3.0.co;2-7

Cited by 20 publications

(9 citation statements)

References 14 publications

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“…This method resulted in the simultaneous hydrolysis of the acetate to provide diol 34 . For the construction of the cis ‐tetrahydropyrane unit of 5 , we first explored the iodocyclization34 reaction of 34 . However, iodocyclization of diol 34 with iodine in acetonitrile yielded a complex mixture (Table 1, entry 1), probably due to the lability of the acetonide to the HI generated during the cyclization process.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Phorboxazole B

Zhang

Sun

et al. 2006

Chemistry A European J

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An efficient and highly convergent total synthesis of the potent antitumor agent phorboxazole B has been achieved. The synthetic strategy of this synthesis features: 1) a highly efficient substrate-controlled hydrogenation to construct the functionalized cis-tetrahydropyrane unit; 2) iterative crotyl addition to synthesize the segment that contains alternating hydroxyl and methyl substituents; 3) Hg(OAc)2/I2-induced cyclization to establish the cis-tetrahydropyrane moiety; 4) 1,3-asymmetric induction in the Mukaiyama aldol reaction to afford the stereogenic centers at C9 and C3; and 5) the exploration of the Still-Gennari olefination reaction to complete the macrolide ring of phorboxazoloe B.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Phorboxazole B

Zhang

Sun

et al. 2006

Chemistry A European J

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“…This mechanistic interpretation applies to cases in which the allylic and homoallylic substituents belong to a cyclohexane [153].…”

Section: 182mentioning

confidence: 96%

Carbometallation Reactions

Marek¹,

and²,

Banon-Tenne³

2004

Metal‐Catalyzed Cross‐Coupling Reactions

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“…1 This class of compounds can be easily prepared from the corresponding 1,2-disubstituted homopropargylic alcohols 2. We were thus in need of a simple and totally stereoselective access to compounds 2.…”

Section: Homopropargylic Alcohols As Interesting Targetsmentioning

confidence: 99%

“…Some years ago, we wanted to study the diastereoselectivity in the addition of allylzinc reagents on g,d-disubstituted vinylmetals 1 (Scheme 1). 1 This class of compounds can be easily prepared from the corresponding 1,2-disubstituted homopropargylic alcohols 2. We were thus in need of a simple and totally stereoselective access to compounds 2.…”

Section: Homopropargylic Alcohols As Interesting Targetsmentioning

confidence: 99%

“…The impact of the BF 3 •OEt 2 activation on the regioselectivity of the reaction could also be evidenced by the ringopening of unsubstituted acetylenic oxiranes. For example, 1 the reaction of acetylenic oxirane 9 with i-PrMgCl leads only to homopropargylic alcohol 10. The possible (and theoretically favored due to steric hindrance) regioisomer 11 was not observed (Scheme 6).…”

Section: Scheme 5 Kinetic Resolution Of Acetylenic Oxiranes Through Ringopeningmentioning

confidence: 99%

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Highly Diastereoselective Syntheses of Propargylic Acid and Homopropargylic Systems

Ferreira¹,

Denichoux²,

Chemla³

et al. 2004

Synlett

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The results of our research dealing with the stereoselective synthesis of propargylic and homopropargylic systems are summarized. In a first part, the stereoselective formation of syn-or anti-disubstituted homopropargylic alcohols from acetylenic oxiranes through S N 2 or double S N 2¢ has been developed. Thus, the two diastereomers of a given homopropargylic alcohol are stereospecifically available. The great impact of Lewis acid activation on the regioselectivity of the ring-opening reactions of propargylic oxiranes is also detailed. In a second part, the preparation and uses of new acetylenic/allenic carbenoids are overviewed; their reactivity towards carbonyl compounds and imines is examined, leading to the highly stereoselective synthesis of acetylenic chlorohydrins, oxiranes and aziridines.

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Diastereoselectivity in the Addition of Allylzinc Reagents to δ-Alkoxy-γ,δ-disubstituted Alkenyllithium Compounds

Cited by 20 publications

References 14 publications

Total Synthesis of Phorboxazole B

Total Synthesis of Phorboxazole B

Carbometallation Reactions

Highly Diastereoselective Syntheses of Propargylic Acid and Homopropargylic Systems

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