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    1,6-Asymmetric Induction by Reductive Acetal Cleavage of a Bicyclic Acetal Using a Sulfinyl Chiral Auxiliary.
    Chemical and Pharmaceutical Bulletin (1998)
    Naoyoshi MaezakiTakeshi ShogakiTuneaki IMAMURAKatsuya TOKUNOKazumi OhkuboTatsuaki TANAKAC. IWATA
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    Abstract:
    A new synthetic route to a chiral 2, 5-disubstituted tetrahydropyran has been achieved by asymmetric reductive acetal cleavage of a bicyclic acetal having a chiral sulfinyl group as a chiral auxiliary. It was found that the (5S)-tetrahydropyran was obtained preferentially (up to 96 : 4) with an R-sulfinyl chiral auxiliary by an efficient 1, 6-asymmetric induction from sulfinyl chirality to the prochiral center on the bicyclic ring.
    Keywords:
    Tetrahydropyran
    Asymmetric induction
    Chiral auxiliary
    Cleavage (geology)
    Chirality
    Topics:
    Synthetic Organic Chemistry Methods
    Asymmetric Synthesis and Catalysis
    Asymmetric Hydrogenation and Catalysis
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    1,6-Asymmetric Induction by Reductive Acetal Cleavage of a Bicyclic Acetal Using a Sulfinyl Chiral Auxiliary.
    Chemical and Pharmaceutical Bulletin (1998)
    Naoyoshi MaezakiTakeshi ShogakiTuneaki IMAMURAKatsuya TOKUNOKazumi Ohkubo
    A new synthetic route to a chiral 2, 5-disubstituted tetrahydropyran has been achieved by asymmetric reductive acetal cleavage of a bicyclic acetal having a chiral sulfinyl group as a chiral auxiliary. It was found that the (5S)-tetrahydropyran was obtained preferentially (up to 96 : 4) with an R-sulfinyl chiral auxiliary by an efficient 1, 6-asymmetric induction from sulfinyl chirality to the prochiral center on the bicyclic ring.
    Tetrahydropyran
    Asymmetric induction
    Chiral auxiliary
    Cleavage (geology)
    Chirality
    Citations (4)
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    Tetrahedron Letters (1996)
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    Journal of the Chemical Society Chemical Communications (1992)
    C. IWATANaoyoshi MaezakiManabu MurakamiMotohiro SoejimaTetsuaki Tanaka
    The novel asymmetric functionalisation of a prochiral 1,3-diol is accomplished by the diastereoselective C–O bond fission of the chiral β-arylsulfinyl acetal via two types of chelation controlled transition states (A and C in Scheme 4).
    Asymmetric induction
    Citations (15)
    Diastereoselective Synthesis of Highly Functionalized Tetrahydropyrans from the Cyclic Vinyl Acetal with Aldehydes Mediated by Lewis Acid Catalyst
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    The structure of bicyclic ferrocenylmethylene substituted 2-pyrazolines and their reactions with azodicarboxylic acid N-phenylimide
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    Remote asymmetric induction for chiral 1,4-diols using a chiral acetal derived from chiral hydrobenzoin
    Tetrahedron Letters (1996)
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    Asymmetric induction
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    Stereoselective synthesis of a chiral synthon, 2,2,5-trisubstituted tetrahydropyran, based on simultaneous 1,3- and 1,6-asymmetric induction via nucleophilic acetal cleavage reaction of the bicyclic acetal: a total synthesis of (−)-malyngolide
    Chemical Communications (1997)
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    A new approach to remote asymmetric induction in the diastereoselective reduction of γ-keto esters by use of a chiral podand as chiral auxiliary
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    Chiral auxiliary
    Chiral derivatizing agent
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    Synthesis (1988)
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    Tetrahydropyran
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    Stereoselective synthesis of a 2,2,5-trisubstituted tetrahydropyran chiron via 1,3- and 1,6-asymmetric induction: A total synthesis of (−)-malyngolide
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    Asymmetric induction
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