CAMPHOR-DERIVED 2-STANNYL-N-BOC-1,3-OXAZOLIDINE - A NEW CHIRAL FORMYLANION EQUIVALENT FOR THE ASYMMETRIC-SYNTHESIS OF 1,2-DIOLS

被引：51

作者：

COLOMBO, L

DIGIACOMO, M

BRUSOTTI, G

MILANO, E

机构：

[1] Dipartimento di Chimica Farmaceutica, Università di Pavia, I-27100 Pavia

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 16期

关键词：

D O I：

10.1016/0040-4039(95)00369-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure 2-tributylstannyl-N-Boc-1,3-oxazolidine 6, prepared from the camphor-derived aminoalcohol 5, was converted to diastereomerically pure 2-acyl derivatives 8 in three steps. Reaction of these ketones with Grignard reagents at -78 degrees C proceeded with high stereoselectivity affording tertiary carbinols which gave 1,2-diols with >96% ee after hydrolysis and reduction of the intermediate a-hydroxy aldehydes. A new deblocking procedure of the t-Boc group is also described.

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页码：2863 / 2866

页数：4

相关论文

共 20 条

[1] ASYMMETRIC-SYNTHESIS OF HOMOCHIRAL 1,2-DIOLS VIA N-BOC OXAZOLIDINES [J].

AGAMI, C ;

COUTY, F ;

LEQUESNE, C .

TETRAHEDRON LETTERS, 1994, 35 (20) :3309-3312

[2] CHIRAL 2-LITHIO-1,3-DIOXOLANES AND 2-LITHIOOXAZOLIDINES - NEW FORMYL ANION EQUIVALENTS [J].

COLOMBO, L ;

DIGIACOMO, M ;

BRUSOTTI, G ;

DELOGU, G .

TETRAHEDRON LETTERS, 1994, 35 (13) :2063-2066

[3] LOSS OF THE TERT-BUTYLOXYCARBONYL (BOC) PROTECTING GROUP UNDER BASIC CONDITIONS [J].

CURRAN, TP ;

POLLASTRI, MP ;

ABELLEIRA, SM ;

MESSIER, RJ ;

MCCOLLUM, TA ;

ROWE, CG .

TETRAHEDRON LETTERS, 1994, 35 (30) :5409-5412

[4] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[5] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[6] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[7]

DONDONI A, 1993, ADV USE SYNTHONS ORG, P1

[8] ALPHA-TRIBUTYLSTANNYLACETALS - PREPARATION VIA TRANSACETALIZATION OF DIETHOXYMETHYLTRIBUTYLTIN, AND USE FOR THE SYNTHESIS OF NEW ALPHA-STANNYLATED ETHERS [J].

DUCHENE, A ;

BOISSIERE, S ;

PARRAIN, JL ;

QUINTARD, JP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 387 (02) :153-162

[9] ASYMMETRIC SYNTHESIS OF NEARLY OPTICALLY PURE ATROLACTIC ACID METHYL-ETHER [J].

ELIEL, EL ;

FRAZEE, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (20) :3598-3599

[10]

ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125