Stereospecific Pseudorotation of Diastereomeric Anti‐Apicophilic Spirophosphoranes: A Novel Stereochemical Transformation Involving 10‐P‐5 Phosphoranes | Zendy

Kojima Satoshi | Zendy; Nakamoto Masaaki | Zendy; Akiba Kinya | Zendy

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Stereospecific Pseudorotation of Diastereomeric Anti‐Apicophilic Spirophosphoranes: A Novel Stereochemical Transformation Involving 10‐P‐5 Phosphoranes

Author(s) -

Kojima Satoshi,

Nakamoto Masaaki,

Akiba Kinya

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200700968

Subject(s) - diastereomer , chemistry , phosphorane , stereospecificity , pseudorotation , stereochemistry , organic chemistry , ring (chemistry) , catalysis

A diastereomeric pair of monocyclic apical H‐phosphoranes ( 2‐ exo and 2‐ exo ) has been prepared from a diastereomeric pair of bicyclic equatorial H‐spirophosphoranes ( 1 ) with t BuLi. The thermal cyclization reaction of each diastereomeric apical H‐phosphorane gave rise to different diastereomeric O ‐equatorial anti‐apicophilic phosphoranes ( 3‐ exo and 3‐ endo , respectively) as single products. On the other hand, the oxidation reaction of each of these apical H‐phosphoranes was complementary to the thermal reaction, affording the opposite diastereomeric anti‐apicophilic phosphorane ( 3‐ endo and 3‐ exo , respectively) as a single product. The pseudorotation of each of these diastereomeric anti‐apicophilic phosphoranes ( 3‐ exo and 3‐ endo ) gave rise to different diastereomeric O ‐apical phosphoranes ( 4‐ exo and 4‐ endo , respectively) as single products.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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