Ring Opening of Epoxides by Pendant Silanols
We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by
either Ph3C+ BF4–or BINOL-phosphoric acid. Silanol epoxides derived from trans-allylic …
either Ph3C+ BF4–or BINOL-phosphoric acid. Silanol epoxides derived from trans-allylic …
Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N …
We present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of
aziridines with pendant silanols is compatible with a range of substrates. To engage …
aziridines with pendant silanols is compatible with a range of substrates. To engage …
Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols
We present protocols for the highly regioselective hydroxyselenylation and
silanoxyselenylation of allylic silanols. N-(Phenylseleno) phthalimide acts as the …
silanoxyselenylation of allylic silanols. N-(Phenylseleno) phthalimide acts as the …
Covalent tethers for precise amino alcohol syntheses: ring opening of epoxides by pendant sulfamates and sulfamides
We describe the development of the first ring opening of epoxides using pendant sulfamates
and sulfamides. These reactions are promoted by a base and proceed under mild conditions …
and sulfamides. These reactions are promoted by a base and proceed under mild conditions …
Ring Opening of Aziridines by Pendant Silanols Allows for Stereospecific Preparations of 1′-Amino-tetrahydrofurans
We have developed a highly stereospecific cyclization of aziridine silanols into 1′-amino-
tetrahydrofurans. Our protocol of stirring a substrate with 10 mol% Sc (OTf) 3 and 1 …
tetrahydrofurans. Our protocol of stirring a substrate with 10 mol% Sc (OTf) 3 and 1 …
Dancing silanols: stereospecific rearrangements of silanol epoxides into silanoxy-tetrahydrofurans and silanoxy-tetrahydropyrans
We have developed highly stereospecific rearrangements of silanol epoxides into 1′-
silanoxy-tetrahydrofurans and 1′-silanoxy-tetrahydropyrans. Upon treatment with Ph3CBF4 …
silanoxy-tetrahydrofurans and 1′-silanoxy-tetrahydropyrans. Upon treatment with Ph3CBF4 …
Taming Tethered Nitreniums for Alkene Functionalization Reactions
We present the first examples of amino-trifluoroacetoxylations of alkenes using N-alkoxy
carbamate tethers. Hypervalent iodine oxidants mediate this transformation, providing a …
carbamate tethers. Hypervalent iodine oxidants mediate this transformation, providing a …
Highly Stereospecific Cyclizations of Homoallylic Silanols
We demonstrate that di-tert-butylsilanols are competent nucleophiles for the intramolecular
interception of palladium π-allyl species. In these reactions, allyl ethyl carbonates are the …
interception of palladium π-allyl species. In these reactions, allyl ethyl carbonates are the …
Fun With Unusual Functional Groups: Sulfamates, Phosphoramidates, and Di‐tert‐butyl Silanols
S Sathyamoorthi - European Journal of Organic Chemistry, 2024 - Wiley Online Library
Compared to ubiquitous functional groups such as alcohols, carboxylic acids, amines, and
amides, which serve as central “actors” in most organic reactions, sulfamates …
amides, which serve as central “actors” in most organic reactions, sulfamates …
Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective
We present the first racemic and scalemic examples of di-tert-butyl silanoxy-Michael
additions. Our operationally simple protocol is selective for nitro-olefins and simply involves …
additions. Our operationally simple protocol is selective for nitro-olefins and simply involves …