Preparation of Tributyl(iodomethyl)stannane

Luescher, Michael U.; Jindakun, Chalupat; Bode, Jeffrey W.

doi:10.15227/orgsyn.095.0345

Cited by 2 publications

(3 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Given these results, a variety of electrophiles were screened (see the Supporting Information). To our surprise, iodomethyltri- n -butylstannane was the sole electrophile that successfully alkylated 22 . With the stannyl ether derivative 24 in hand, we could interrogate the [2,3]-Wittig rearrangement via application of the Still variant of this sigmatropic rearrangement.…”

Section: Resultsmentioning

confidence: 91%

Enantioselective Syntheses of Wickerols A and B

et al. 2023

View full text Add to dashboard Cite

The evolution of a successful strategy for the synthesis of the strained, cage-like antiviral diterpenoids wickerols A and B is described. Initial attempts to access the carbocyclic core were surprisingly challenging and in retrospect, presaged the many detours needed to ultimately arrive at the fully adorned wickerol architecture. In most cases, conditions to trigger desired outcomes with respect to both reactivity and stereochemistry were hard-won. The successful synthesis ultimately leveraged alkenes in virtually all productive bond-forming events. A series of conjugate addition reactions generated the fused tricyclic core, a Claisen rearrangement was used to install an otherwise unmanageable methyl-bearing stereogenic center, and a Prins cyclization closed the strained bridging ring. This final reaction proved enormously interesting because the strain of the ring system permitted diversion of the presumed initial Prins product into several different scaffolds.

show abstract

Section: Resultsmentioning

confidence: 91%

Enantioselective Syntheses of Wickerols A and B

et al. 2023

View full text Add to dashboard Cite

show abstract

“…The resulting suspension was allowed to warm to rt. After 60 min, the reaction mixture was re-cooled to 0 °C and tributyl(iodomethyl)stannane 5 (1.96 g, 4.56 mmol, 1.20 equiv) was added dropwise over 10 min. The resulting suspension was allowed to warm to r.t. over 3 h and stirred at r.t. for 3 h. The reaction mixture was cooled to 0 °C and slowly quenched with sat aq NH4Cl (50 mL).…”

Section: -(((Tributylstannyl)methoxy)methyl)-n-tritylcyclopropan-1-amine (13)mentioning

confidence: 99%

“…1065 cm -1 ; 1 H NMR (400 MHz, CDCl3): δ 8.31 (s, 2H), 7.82 (d, J = 8.0 Hz, 4H), 7.64 (d, J = 8.2 Hz, 4H), 3.78 (s, 8H), 3.63 (s, 4H); 13 C NMR(100 MHz, CDCl3): δ 161.3, 139.4 (q, JCF = 1.50 Hz), 132.4 (q, JCF = 32.4 Hz), 128 5,. 125.6 (q, JCF …”

mentioning

confidence: 99%

Evidence for a Radical Mechanism in Cu(II)-Promoted SnAP Reactions

Luescher¹,

Bode

2019

Synlett

Self Cite

View full text Add to dashboard Cite

Saturated nitrogen heterocycles can be found with increasing abundance in bioactive molecules despite a limited number of methods to access these scaffolds. However, the coupling of recently introduced SnAP [tin (Sn) amine protocol] reagents with a wide range of aldehydes and ketones has proven to be a reliable, practical, and versatile one-step approach to saturated N-heterocycles. While effective, the lack of mechanistic understanding limits efforts to develop new catalytic and enantioselective variants. To distinguish between a polar or radical mechanism, we assessed Lewis and Brønsted acids, radical trapping experiments, and radical clock SnAP reagents reinforcing the current understanding of the SnAP protocol as a radical cyclization.

show abstract

Preparation of Tributyl(iodomethyl)stannane

Cited by 2 publications

References 18 publications

Enantioselective Syntheses of Wickerols A and B

Enantioselective Syntheses of Wickerols A and B

Evidence for a Radical Mechanism in Cu(II)-Promoted SnAP Reactions

Contact Info

Product

Resources

About