31350-92-2Relevant academic research and scientific papers
Chain Extension of Boronic Esters with Lithiooxiranes Generated by Sulfoxide-Metal Exchange - Stereocontrolled Access to 2°/2°, 2°/3°, and 3°/3° Vicinal Diols and Related Compounds
Alwedi, Embarek,Zakharov, Lev N.,Blakemore, Paul R.
supporting information, p. 6643 - 6648 (2016/02/19)
Lithiooxiranes [LiCR1(O)CR2R3, R1 = H, Me; R2/R3 = H/Ph, H/tBu, Me/Ph], generated by sulfoxide-lithium exchange from stereodefined sulfinyl epoxides (with use of PhLi or tBuLi, THF, at or below -90 °C), were employed for the stereospecific reagent-controlled homologation of boronic esters R0-Bpin (R0 = BnCH2, allyl, cHex, Ph). Addition of TBSOTf to the intermediate ate complexes gave β-silyloxyboronates that were converted to vicinal diol monosilyl ethers by oxidative work-up with aq. NaOOH. The 2°/2° (4-32 %, dr > 98:2), 2°/3° (21-66 %, dr ≥ 65:35), and 3°/3° (59-68 %, dr ≥ 95:5) contiguous stereodiad-containing compounds created in this manner were typically obtained in a highly stereocontrolled manner. In general, cis-sulfinyl epoxides afforded anti-like stereodiads, whereas trans-sulfinyl epoxides afforded syn-like stereodiads; however, as a result of its suspected configurational instability, LiCMe(O)CHPh gave anti-like 2°/3° motifs regardless of sulfinyl epoxide stereochemistry.
THE PRACTICAL PROCEDURE FOR A PREPARATION OF 1-CHLOROALKYL p-TOLYL SULFOXIDES IN HIGH OPTICALLY ACTIVE FORM: A VERY SHORT SYNTHESIS OF OPTICALLY ACTIVE DISPARLURE
Satoh, Tsuyoshi,Oohara, Teruhiko,Ueda, Yoshiko,Yamakawa, Koji
, p. 313 - 316 (2007/10/02)
A chlorination of optically active alkyl p-tolyl sulfoxides with N-chlorosuccinimide in dichloromethane in the presence of potassium carbonate afforded optically active 1-chloroalkyl p-tolyl sulfoxides in 87-94percent ee (88-94percent chemical yields).The optically active chloroalkyl sulfoxide was applied to a synthesis of optically active (+)-disparlure.
