Reactions of (RP)- and (SP)-tert-butylphenylphosphinobromidates and tert-butylphenylthionophosphinochloridates with heteroatom nucleophiles;: preparation of P-chiral binol phosphinates and related compounds

被引：50

作者：

Au-Yeung, TL ^{[1
]}

Chan, KY ^{[1
]}

Chan, WK ^{[1
]}

Haynes, RK ^{[1
]}

Williams, ID ^{[1
]}

Yeung, LL ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 03期

关键词：

D O I：

10.1016/S0040-4039(00)01950-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of (R-P)- and (S-P)-tert-butylphenylphosphinobromidates and tert-butylphenylthionophosphinochloridates with metallated phenol and BINOL alkoxides, thioalkoxides, amides and enolates leading with clean inversion at phosphorus to phosphinates, phosphinothiolates and phosphinoamidates, and the corresponding thionophosphorus compounds are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：453 / 456

页数：4

共 11 条

[1] (R)- and (S)-6,6'-dimethyl- and 6,6'-dimethoxy-2,2'-diiodo-1,1'-biphenyls: Versatile intermediates for the synthesis of atropisomeric diphosphine ligands [J].

Cereghetti, M ;

Arnold, W ;

Broger, EA ;

Rageot, A .

TETRAHEDRON LETTERS, 1996, 37 (30) :5347-5350

[2] High symmetry chiral auxiliaries containing heteroatoms [J].

DeLucchi, O .

PURE AND APPLIED CHEMISTRY, 1996, 68 (04) :945-949

[3] Stereoselective preparation of functionalized tertiary P-chiral phosphine oxides by nucleophilic addition of lithiated tert-butylphenylphosphine oxide to carbonyl compounds. [J].

Haynes, RK ;

Lam, WWL ;

Yeung, LL .

TETRAHEDRON LETTERS, 1996, 37 (27) :4729-4732

[4] PREPARATION OF ENANTIOMERICALLY PURE TERTIARY PHOSPHINE OXIDES FROM, AND ASSAY OF ENANTIOMERIC PURITY WITH, (R(P))-TERT-BUTYLPHENYLPHOSPHINOTHIOIC AND (S-P)-TERT-BUTYLPHENYLPHOSPHINOTHIOIC ACIDS [J].

HAYNES, RK ;

FREEMAN, RN ;

MITCHELL, CR ;

VONWILLER, SC .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :2919-2921

[5] The first examples of enantiomerically pure diphosphane dioxides (R-P,R-P)- and (S-P,S-P)-1,2-di-tert-butyl-1,2-diphenyldiphosphane 1,2-dioxides, and (R-P)- and (S-P)-1-tert-butyl-1,2,2-triphenyldiphosphane 1,2-dioxides [J].

Haynes, RK ;

Lam, WWL ;

Williams, ID ;

Yeung, LL .

CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (12) :2052-2057

[6] Asymmetric synthesis of organophosphorus compounds [J].

Kolodiazhnyi, OI .

TETRAHEDRON-ASYMMETRY, 1998, 9 (08) :1279-1332

[7] REACTION OF THIOLO AND SELENOLO ESTERS OF PHOSPHORUS-ACIDS WITH HALOGENS .2. INTERACTION OF S-METHYL TERT-BUTYL(PHENYL)PHOSPHINOTHIOLATES AND DI-TERT-BUTYL-PHOSPHINOTHIOLATES WITH ELEMENTAL BROMINE AND IODINE [J].

KRAWIECKA, B ;

WOJNATADEUSIAK, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (02) :301-309

[8] Preparation of bi- and tridentate doubly P-chiral diphosphine dioxide ligands for asymmetric catalysis [J].

Lam, WWL ;

Haynes, RK ;

Yeung, LL ;

Chan, EWK .

TETRAHEDRON LETTERS, 1996, 37 (27) :4733-4736

[9]

Ohff M, 1998, SYNTHESIS-STUTTGART, P1391

[10] PREPARATION OF SCALEMIC P-CHIRAL PHOSPHINES AND THEIR DERIVATIVES [J].

PIETRUSIEWICZ, KM ;

ZABLOCKA, M .

CHEMICAL REVIEWS, 1994, 94 (05) :1375-1411

← 1 2 →