Ring Opening of Epoxides by Pendant Silanols

S Nagamalla, JT Mague, S Sathyamoorthi - Organic letters, 2022 - ACS Publications
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 …

Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N …

S Nagamalla, D Paul, JT Mague… - Organic letters, 2022 - ACS Publications
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 …

Hydroxyselenylation and Tethered Silanoxyselenylation of Allylic Silanols

H Joshi, S Sathyamoorthi - The Journal of organic chemistry, 2022 - ACS Publications
We present protocols for the highly regioselective hydroxyselenylation and
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

S Nagamalla, JT Mague, S Sathyamoorthi - Organic letters, 2023 - ACS Publications
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 …

Ring Opening of Aziridines by Pendant Silanols Allows for Stereospecific Preparations of 1′-Amino-tetrahydrofurans

AK Nirpal, S Nagamalla, JT Mague… - The Journal of …, 2023 - ACS Publications
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 …

Dancing silanols: stereospecific rearrangements of silanol epoxides into silanoxy-tetrahydrofurans and silanoxy-tetrahydropyrans

H Joshi, AA Thomas, JT Mague… - Organic Chemistry …, 2023 - pubs.rsc.org
We have developed highly stereospecific rearrangements of silanol epoxides into 1′-
silanoxy-tetrahydrofurans and 1′-silanoxy-tetrahydropyrans. Upon treatment with Ph3CBF4 …

Taming Tethered Nitreniums for Alkene Functionalization Reactions

R Silver, AK Nirpal, S Sathyamoorthi - The Journal of Organic …, 2024 - ACS Publications
We present the first examples of amino-trifluoroacetoxylations of alkenes using N-alkoxy
carbamate tethers. Hypervalent iodine oxidants mediate this transformation, providing a …

Highly Stereospecific Cyclizations of Homoallylic Silanols

AH Shinde, RA Dhokale, JT Mague… - The Journal of …, 2022 - ACS Publications
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 …

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 …

Intramolecular Silanoxy-Michael Reactions with Pendant Nitroalkenes: Racemic and Enantioselective

H Joshi, S Sathyamoorthi - The Journal of organic chemistry, 2024 - ACS Publications
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 …