920749-74-2

Upstream product

• 920749-72-0 Allyl-{(S)-5-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-2-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-vinyl]-pentyl}-carbamic acid tert-butyl ester 
• 920749-71-9 (S)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[(E)-2-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-vinyl]-pentylamine 
• 920749-67-3 (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-hept-2-en-1-ol 
• 920749-70-8 [(E)-(S)-5-Azido-7-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-hept-6-enyloxy]-tert-butyl-diphenyl-silane 
• 920749-73-1 Allyl-{(S)-5-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-2-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-vinyl]-pentyl}-amine 
• 371172-65-5 (E)-tert-butyl(6-iodohex-5-en-1-yloxy)diphenylsilane 

Downstream Products

• 1042908-30-4 C₂₉H₄₁NO₄Si 

Relevant academic research and scientific papers

Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: Application to the total syntheses of alkaloids

(Chemical Equation Presented) We describe a tandem Mitsunobu/3,3- sigmatropic rearrangement of allylic azides on a chiral auxiliary system that favors one regioisomer thanks to its exceptional steric bias. The sequence may be completed by the oxidative cleavage of the auxiliary or by a ring-closing metathesis reaction that produces a carbo-or heterocycle directly and a recyclable form of the chiral auxiliary. Applications of the methodology to the total synthesis of (+)-coniine, (+)-lentiginosin, and (+)-pumiliotoxin C are reported.

Cleavage of a chiral auxiliary using RCM on an especially sterically crowded alkene: Syntheses of chiral carbo- and heterocycles

Chiral 1,5-, 1,6-, and 1,7-dienes generated in 3-4 steps from chiral auxiliary p-menthane-3-carboxaldehyde undergo RCM with notable discrepancies in reactivity depending on the nature and number of substituents flanking the central double bond. The chiral